The Journal of Organic Chemistry
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ether = 1:50) afforded 3f as a colorless oil (33.9 mg, 80% yield); TLC
(PE:EA, 10:1 v/v): Rf = 0.65; 1H NMR (400 MHz, CDCl3) δ 7.82−
7.80 (m, 2H), 7.61−7.57 (m, 1H), 7.50−7.46 (m, 2H), 7.40−7.32
(m, 3H), 7.15−7.12 (m, 1H), 3.86 (s, 3H); 13C{1H} NMR (100
MHz, CDCl3) δ 196.5, 159.6, 138.9, 137.6, 132.4, 130.0, 129.2,
128.2122.8, 118.8, 114.3, 55.4.
7.54−7.50 (m, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 195.2,
2
138.2, 136.7, 133.1, 133.0, 131.0 (q, JC‑F = 32.8 Hz), 130.0, 128.9,
3
3
128.8 (q, JC‑F = 3.7 Hz), 128.5, 126.7 (q, JC‑F = 3.7 Hz), 123.7 (q,
1JC‑F = 270.8 Hz); 19F NMR δ −62.74 (s, 3F).
(4-Fluorophenyl)(phenyl)methanone (3o).25 Purification by col-
umn chromatography on a silica gel (ethyl acetate:petroleum ether =
1:50) afforded 3o as a white solid (30.1 mg 75% yield), mp 45−47 °C
(lit.28 46−48 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.65; 1H NMR (400
MHz, CDCl3) δ 7.87−7.83 (m, 2H), 7.78−7.76 (m, 2H), 7.62−7.58
(m, 1H), 7.51−7.47 (m, 2H), 7.19−7.14 (m, 2H); 13C{1H} NMR
(100 MHz, CDCl3) δ 195.2, 165.4 (d, 1J = 252.5 Hz), 137.5, 133.8 (d,
Benzophenone (3g).25 Purification by column chromatography on
a silica gel (ethyl acetate:petroleum ether = 1:50) afforded 3g as a
white solid (31.7 mg, 87% yield), mp 47−48 °C (lit.24 48−49 °C);
1
TLC (PE:EA, 10:1 v/v): Rf = 0.55; H NMR (400 MHz, CDCl3) δ
7.82−7.80 (m, 4H), 7.62−7.57 (m, 2H), 7.51−7.47 (m, 4H);
13C{1H} NMR (100 MHz, CDCl3) δ 196.7, 137.6, 132.4, 130.0,
128.3.
4JC‑F = 3.0 Hz), 132.6 (d, JC‑F = 9.1 Hz), 132.4, 129.9, 128.3, 115.4
3
(d, JC‑F = 21.7 Hz); 19F NMR δ −105.9 (s, 1F).
2
(4-Chlorophenyl)(phenyl)methanone (3p).25 Purification by
column chromatography on a silica gel (ethyl acetate:petroleum
ether = 1:50) afforded 3p as a white solid (32.8 mg, 76% yield), mp
75−77 °C (lit.28 73−74 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.65; 1H
NMR (400 MHz, CDCl3) δ 7.79−7.74 (m, 4H), 7.62−7.58 (m, 1H),
7.51−7.45 (m, 4H); 13C{1H} NMR (100 MHz, CDCl3) δ 195.5,
138.9, 137.2, 135.8, 132.6, 131.4, 129.9, 128.6, 128.4.
(1,1′-Biphenyl)-4-yl(phenyl)methanone (3h).27 Purification by
column chromatography on a silica gel (ethyl acetate:petroleum
ether = 1:50) afforded 3h as a yellow solid (43.9 mg, 85% yield), mp
101−102 °C (lit.27 100.7−101.5 °C); TLC (PE:EA, 10:1 v/v): Rf =
1
0.55; H NMR (400 MHz, CDCl3) δ 7.90 (d, J = 7.7 Hz, 2H), 7.85
(d, J = 8.0 Hz, 2H), 7.71 (d, J = 7.7 Hz, 2H), 7.66 (d, J = 8.0 Hz, 2H),
7.61−7.59 (m, 1H), 7.53−7.47 (m, 4H), 7.43−7.41 (m, 1H);
13C{1H} NMR (100 MHz, CDCl3) δ 196.3, 145.2, 140.0, 137.7,
136.2, 132.3, 130.7, 130.0, 128.9, 128.3, 128.2, 127.3, 126.9.
(4-Bromophenyl)(phenyl)methanone (3q).25 Purification by
column chromatography on a silica gel (ethyl acetate:petroleum
ether = 1:50) afforded 3q as a white solid (38.6 mg, 74% yield), mp
78−80 °C (lit.30 79−80 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.65; 1H
NMR (400 MHz, CDCl3) δ 7.78−7.74 (m, 2H), 7.62−7.58 (m, 5H),
7.51−7.45 (m, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 195.6,
137.2, 136.3, 132.7, 131.6, 131.5, 129.9, 128.4, 127.5.
1-(4-Benzoylphenyl)ethanone (3i).28 Purification by column
chromatography on a silica gel (ethyl acetate:petroleum ether =
1:50) afforded 3i as a white solid (33.1 mg, 74% yield), mp 81−83 °C
(lit.28 83−84 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.2; H NMR (400
1
MHz, CDCl3) δ 8.07−8.05 (m, 2H), 7.88−7.86 (m, 2H), 7.82−7.80
(m, 2H), 7.65−7.61 (m, 1H), 7.53−7.49 (m, 2H), 2.67 (s, 3H);
13C{1H} NMR (100 MHz, CDCl3) δ 197.5, 196.0, 141.3, 139.6,
136.9, 133.0, 130.1, 130.0, 128.5, 128.1, 26.9.
(Naphthalen-6-yl)(phenyl)methanone (3r).28 Purification by
column chromatography on a silica gel (ethyl acetate:petroleum
ether = 1:50) afforded 3r as a white solid (32.5 mg, 70% yield), mp
80−82 °C (lit.28 81−83 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.5; H
1
4-Benzoylbenzaldehyde (3j).28 Purification by column chroma-
tography on a silica gel (ethyl acetate:petroleum ether = 1:50)
afforded 3j as a white solid (33.6 mg, 80% yield), mp 62−64 °C (lit.28
62−65 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.65; 1H NMR (400 MHz,
CDCl3) δ 10.13 (s, 1H), 8.0 (d, J = 8.3 Hz, 2H), 7.92 (d, J = 8.0 Hz,
2H), 7.82−7.79 (m, 2H), 7.65−7.61 (m, 1H), 7.53−7.49 (m, 2H);
13C{1H} NMR (100 MHz, CDCl3) δ 195.8, 191.6, 142.5, 138.4,
136.7, 133.1, 130.3, 130.1, 129.5, 128.5.
NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.95−7.86 (m, 6H), 7.65−
7.50 (m, 5H); 13C{1H} NMR (100 MHz, CDCl3) δ 196.7, 137.9,
135.3, 134.8, 132.4, 132.2, 131.8, 130.1, 129.4, 128.34, 128.31, 128.29,
127.8, 126.8, 125.8.
(6-Fluoropyridin-3-yl)(phenyl)methanone (3s).16 Purification by
column chromatography on a silica gel (ethyl acetate:petroleum ether
= 1:50) afforded 3s as a white solid (17.4 mg, 43% yield), mp 42−44
°C; TLC (PE:EA, 10:1 v/v): Rf = 0.25; 1H NMR (400 MHz, CDCl3)
δ 8.66 (d, J = 2.3 Hz, 1H), 8.32−8.27 (m, 1H), 7.81−7.79 (m, 2H),
Ethyl 4-Benzoylbenzoate (3k).23 Purification by column chroma-
tography on a silica gel (ethyl acetate:petroleum ether = 1:50)
afforded 3k as a yellow oil (46.3 mg, 90% yield); TLC (PE:EA, 10:1
7.67−7.63 (m, 1H), 7.55−7.51 (m, 2H), 7.09 (dd, J1 = 8.7, 2.7 Hz,
1
1H); 13C{1H} NMR (100 MHz, CDCl3) δ 193.2, 165.2 (d, JC‑F
=
1
244.3 Hz), 150.3 (d, 3JC‑F = 16.1 Hz), 142.8 (d, 3JC‑F = 9.1 Hz), 136.6,
133.2, 131.4 (d, JC‑F = 4.5 Hz), 129.8, 128.6, 109.7 (d, JC‑F = 37.1
v/v): Rf = 0.65; H NMR (400 MHz, CDCl3) δ 8.12 (d, J = 8.3 Hz,
4
2
2H), 7.85−7.79 (m, 4H), 7.64−7.60 (m, 1H), 7.52−7.48 (m, 2H),
4.43 (q, J = 7.2 Hz, 2H), 1.43 (t, J = 7.2 Hz, 3H); 13C{1H} NMR
(100 MHz, CDCl3) δ 196.0, 165.8, 141.2, 137.0, 133.6, 132.9, 130.1,
129.7, 129.4, 128.4, 61.4, 14.3.
Hz); 19F NMR δ −61.45 (s, 1F).
4-Methoxy-4′-methylbenzophenone (3b′).31 Purification by
column chromatography on a silica gel (ethyl acetate:petroleum
ether = 1:50) afforded 3b′ as a white solid (44.3 mg, 83% yield), mp
4-Cyanobenzophenone (3l).25 Purification by column chromatog-
raphy on a silica gel (ethyl acetate:petroleum ether = 1:50) afforded 3l
as a white solid (35.5 mg, 85% yield), mp 111−112 °C (lit.27 110.8−
89−90 °C (lit.31 90−91 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.5; H
1
NMR (400 MHz, DMSO-d6) δ 7.73 (d, J = 8.6 Hz, 2H), 7.60 (d, J =
7.8 Hz, 2H), 7.35 (d, J = 7.7 Hz, 2H), 7.08 (d, J = 8.6 Hz, 2H), 3.85
(s, 3H), 2.40 (s, 3H); 13C{1H} NMR (100 MHz, DMSO-d6) δ 194.1,
162.7, 142.4, 135.0, 132.0, 129.6, 129.5, 129.0, 113.8, 55.5, 21.1.
Mesityl(p-tolyl)methanone (3c′).16 Purification by column chro-
matography on a silica gel (ethyl acetate:petroleum ether = 1:50)
afforded 3c′ as a white solid (34.8 mg, 73% yield), mp 39−40 °C
1
111.1 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.5; H NMR (400 MHz,
CDCl3) δ 7.88 (d, J = 8.0 Hz, 2H), 7.81−7.72 (m, 4H), 7.66−7.63
(m, 1H), 7.54−7.50 (m, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ
195.0, 141.2, 136.3, 133.3, 132.2, 130.2, 130.1, 128.6, 118.0, 115.7.
Phenyl(4-(trifluoromethyl)phenyl)methanone (3m).23 Purifica-
tion by column chromatography on a silica gel (ethyl acetate:petro-
leum ether = 1:50) afforded 3m as a white solid (44.5 mg, 88% yield),
mp 111−112 °C (lit.28 110−112 °C); TLC (PE:EA, 10:1 v/v): Rf =
0.65; 1H NMR (400 MHz, CDCl3) δ 7.90 (d, J = 8.0 Hz, 2H), 7.82−
7.80 (m, 2H), 7.76 (d, J = 8.0 Hz, 2H), 7.66−7.61 (m, 1H), 7.54−
7.49 (m, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 195.7, 140.9,
136.9, 133.9 (q, 2JC‑F = 36.6 Hz), 133.2, 130.3, 130.2, 128.7, 125.5 (q,
(lit.32 39−40 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.5; H NMR (400
1
MHz, CDCl3) δ 7.70 (d, J = 8.0 Hz, 2H), 7.24 (d, J = 8.0 Hz, 2H),
6.89 (s, 2H), 2.41 (s, 3H), 2.33 (s, 3H), 2.08 (s, 6H); 13C{1H} NMR
(100 MHz, CDCl3) δ 200.4, 144.5, 138.3, 137.0, 134.8, 134.1, 129.53,
129.46, 128.2, 21.7, 21.1, 19.3.
4-Trifluoromethyl-4′-methylbenzophenone (3d′).31 Purification
by column chromatography on a silica gel (ethyl acetate:petroleum
ether = 1:50) afforded 3d′ as a white solid (5.8 mg, 10% yield), mp
133−135 °C (lit.31 134−135 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.5;
1H NMR (400 MHz, CDCl3) δ 7.87 (d, J = 8.0 Hz, 2H), 7.75−7.71
(m, 4H), 7.30 (d, J = 8.0 Hz, 2H), 2.45 (s, 3H). 13C{1H} NMR (100
MHz, CDCl3) δ 195.2, 144.1, 141.1, 134.1, 133.5 (q, 1JC‑F = 32.5 Hz),
1
3JC‑F = 3.8 Hz), 123.8 (q, JC‑F = 270.9 Hz); 19F NMR δ −63.00 (s,
3F).
Phenyl(3-(trifluoromethyl)phenyl)methanone (3n).25 Purification
by column chromatography on a silica gel (ethyl acetate:petroleum
ether = 1:50) afforded 3n as a white solid (42.8 mg, 85% yield), mp
52−53 °C (lit.29 51−52 °C); TLC (PE:EA, 10:1 v/v): Rf = 0.65; H
1
2
1
NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.98 (d, J = 7.8 Hz, 1H),
7.85 (d, J = 7.8 Hz, 1H), 7.81−7.78 (m, 2H), 7.66−7.61 (m, 2H),
130.3, 130.0, 129.2, 125.2 (q, JC‑F = 3.7 Hz), 123.7 (q, JC‑F = 270.9
Hz), 21.7; 19F NMR δ −63.00 (s, 3F).
5022
J. Org. Chem. 2021, 86, 5016−5025