The Journal of Organic Chemistry
Note
13C{1H} NMR (100 MHz, CDCl3) δ 197.6, 165.7, 140.2, 134.3,
129.8, 128.2, 61.44, 26.9, 14.3.
MHz, CDCl3) δ 197.7, 139.6, 137.5, 130.8, 128.9, 125.6, 124.9, 26.6,
15.6.
1-(2-Methoxyphenyl)ethenone (26). 23 mg, 31% General
Procedure A (14 mg, 18% General Procedure B), colorless oil (PE/
EA 20:1 (v/v)). This compound is known, and the data reported here
are consistent with the literature.26 1H NMR (400 MHz, CDCl3) δ
7.73 (d, J = 7.7 Hz, 1H), 7.47 (t, J = 7.8 Hz, 1H), 6.99 (dd, J = 14.8,
7.9 Hz, 2H), 3.92 (s, 3H), 2.62 (s, 3H). 13C{1H} NMR (100 MHz,
CDCl3) δ 200.0, 158.9, 133.7, 130.4, 128.2, 120.5, 111.5, 56.5, 31.6.
1-(3,4-Dimethylphenyl)ethenone (27). 41 mg, 56% General
Procedure A (38 mg, 51% General Procedure B), colorless oil (PE/
EA 20:1 (v/v)). This compound is known, and the data reported here
are consistent with the literature.33 1H NMR (400 MHz, CDCl3) δ
7.72 (s, 1H), 7.68 (d, J = 7.8 Hz, 1H), 7.20 (d, J = 7.7 Hz, 1H), 2.56
(s, 3H), 2.30 (s, 6H). 13C{1H} NMR (100 MHz, CDCl3) δ 198.1,
142.5, 136.8, 134.9, 129.7, 129.3, 126.0, 77.3, 26.5, 19.9, 19.7.
1-(3,4-Dichlorophenyl)ethenone (28). 49 mg, 52% General
Procedure A (46 mg, 49% General Procedure B), white solid.
Melting point: 74.3−77.1 °C (PE/EA 20:1 (v/v)). This compound is
known, and the data reported here are consistent with the literature.24
1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.76 (d, J = 8.3 Hz, 1H),
7.53 (d, J = 8.3 Hz, 1H), 2.58 (s, 3H). 13C{1H} NMR (100 MHz,
CDCl3) δ 195.6, 137.6, 136.5, 133.2, 130.7, 130.2, 127.3, 26.49.
4-Acetyl-2-chlorobenzonitrile (29). 44 mg, 49% General Proce-
dure A (42 mg, 47% General Procedure B), white solid. Melting
Acetophenone (17). 26 mg, 43% General Procedure A (33 mg,
55% General Procedure B), colorless oil (PE/EA 20:1 (v/v)). This
compound is known, and the data reported here are consistent with
the literature.24 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J = 7.2 Hz,
2H), 7.57 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2 H,), 2.61 (s, 3H).
13C{1H} NMR (100 MHz, CDCl3) δ 197.9, 136.8, 132.9, 128.4,
128.1, 26.4.
1-(3-Fluorophenyl)ethenone (18). 30 mg, 44% General Procedure
A (28 mg, 40% General Procedure B), colorless oil (PE/EA 20:1 (v/
v)). This compound is known, and the data reported here are
consistent with the literature.25 1H NMR (400 MHz, CDCl3) δ 7.75
(d, J = 7.7 Hz, 1H), 7.64 (dd, J = 9.4, 0.8 Hz, 1H), 7.46 (dd, J = 13.6,
7.9 Hz, 1H), 7.30−7.25 (m, 1H), 2.61 (s, 3H). 13C{1H} NMR (100
MHz, CDCl3) δ 196.7, 162.9 (d, J = 247.9 Hz), 139.3 (d, J = 6.0 Hz),
130.3 (d, J = 7.6 Hz), 124.1 (d, J = 2.9 Hz), 120.1 (d, J = 21.5 Hz),
114.9 (d, J = 22.2 Hz), 26.6.
1-(3-Chlorophenyl)ethenone (19). 31 mg, 40% General Procedure
A (28 mg, 36% General Procedure B), colorless oil (PE/EA 20:1 (v/
v)). This compound is known, and the data reported here are
consistent with the literature.28 1H NMR (400 MHz, CDCl3) 7.92 (s,
1H), 7.83 (d, J = 7.7 Hz, 1H), 7.53 (d, J = 8.0 Hz 1H), 7.41 (t, J = 7.8
Hz, 1H), 2.60 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 196.7,
138.5, 134.9, 133.0, 129.9, 128.4, 126.4, 26.7.
1-(3-Bromophenyl)ethenone (20). 39 mg, 40% General Procedure
A (32 mg, 35% General Procedure B), colorless oil (PE/EA 20:1 (v/
v)). This compound is known, and the data reported here are
consistent with the literature.25 1H NMR (400 MHz, CDCl3) δ 8.07
(s, 1H), 7.87 (d, J = 7.8 Hz, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.34 (t, J =
7.9 Hz, 1H), 2.59 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ
196.5, 138.8, 135.9, 131.3, 130.2, 126.8, 122.9, 26.54.
3-Acetylbenzonitrile (21). 28 mg, 39% General Procedure A (25
mg, 34% General Procedure B), white solid. Melting point: 99.1−
100.4 °C (PE/EA 20:1 (v/v)). This compound is known, and the
data reported here are consistent with the literature.25 1H NMR (400
MHz, CDCl3) δ 8.23 (s, 1H), 8.17 (d, J = 7.9 Hz, 1H), 7.84 (d, J =
7.7 Hz, 1H), 7.61 (t, J = 7.8 Hz, 1H), 2.63 (s, 3H). 13C{1H} NMR
(100 MHz, DMSO-d6) δ 196.8, 137.5, 136.5, 132.5, 132.2, 130.1,
118.3, 112.1, 26.9.
1-(3-Acetylphenyl)ethenone (22). 24 mg, 30% General Procedure
A (23 mg, 28% General Procedure B), colorless oil (PE/EA 20:1 (v/
v)). This compound is known, and the data reported here are
consistent with the literature.29 1H NMR (400 MHz, CDCl3) δ 8.51
(s, 1H), 8.14 (d, J = 7.7 Hz, 2H), 7.58 (t, J = 7.7 Hz, 1H), 2.65 (s,
6H). 13C{1H} NMR (100 MHz, CDCl3) δ 197.2, 137.4, 132.4, 129.0,
128.0, 26.6.
Methyl 3-Acetylbenzoate (23). 41 mg, 46% General Procedure A
(36 mg, 40% General Procedure B), white solid. Melting point: 42.0−
43.7 °C (PE/EA 20:1 (v/v)). This compound is known, and the data
reported here are consistent with the literature.30 1H NMR (400
MHz, CDCl3) δ 8.58 (s, 1H), 8.22 (d, J = 7.7 Hz, 1H), 8.14 (d, J =
7.8 Hz, 1H), 7.55 (t, J = 7.8 Hz, 1H), 3.94 (s, 3H), 2.64 (s, 3H).
13C{1H} NMR (100 MHz, CDCl3) δ 197.2, 166.2, 137.2, 133.9,
132.3, 130.6, 129.5, 128.8, 52.4, 26.7.
1-(3-(Benzyloxy)phenyl)ethenone (24). 47 mg, 42% General
Procedure A (38 mg, 34% General Procedure B), colorless oil (PE/
EA 20:1 (v/v)). This compound is known, and the data reported here
are consistent with the literature.31 1H NMR (400 MHz, CDCl3) δ
7.94 (d, J = 8.9 Hz, 2H), 7.46−7.37 (m, 4H), 7.35 (ddd, J = 6.9, 3.6,
1.6 Hz, 1H), 7.01 (d, J = 8.9 Hz, 2H), 5.13 (s, 2H), 2.56 (s, 3H).
13C{1H} NMR (100 MHz, CDCl3) δ 196.8, 162.6, 136.1, 130.6,
130.5, 129.6, 128.7, 128.2, 127.4, 115.3, 114.5, 70.1, 26.3.
1-(3-(Methylthio)phenyl)ethenone (25). 22 mg, 26% General
Procedure A (18 mg, 22% General Procedure B), colorless oil (PE/
EA 20:1 (v/v)). This compound is known, and the data reported here
are consistent with the literature.32 1H NMR (400 MHz, CDCl3) δ
7.81 (s, 1H), 7.69 (d, J = 7.5 Hz, 1H), 7.43 (d, J = 7.8 Hz, 1H), 7.36
(t, J = 7.7 Hz, 1H), 2.59 (s, 3H), 2.52 (s, 3H). 13C{1H} NMR (100
1
point: 134.0−136.3 °C (PE/EA 20:1 (v/v)). H NMR (400 MHz,
CDCl3) δ 8.05 (s, 1H), 7.91 (d, J = 8.0 Hz, 1H), 7.79 (d, J = 8.0 Hz,
1H), 2.63 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 195.3, 140.9,
137.6, 134.4, 129.5, 126.5, 117.1, 115.2, 26.8. HRMS (APCI): m/z
[M + H]+ Calcd for C9H7ClNO+: 180.0211, 182.0182, found:
182.0212, 180.0182.
1-(3-Chloro-4-methylphenyl)ethenone (30). 38 mg, 45% General
Procedure A (35 mg, 41% General Procedure B), white solid. Melting
point: 43.7−44.8 °C (PE/EA 20:1 (v/v)). 1H NMR (400 MHz,
CDCl3) δ 7.82 (s, 1H), 7.63 (d, J = 7.9 Hz, 1H), 7.21 (d, J = 7.9 Hz,
1H), 2.47 (s, 3H), 2.32 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ
196.5, 141.6, 136.2, 134.7, 130.9, 128.8, 126.4, 26.4, 20.2. HRMS
(APCI): m/z [M + H]+ Calcd for C9H10ClO+: 169.0415, 171.0386,
found: 169.0418, 171.0387.
1-(3-Chloro-4-methoxyphenyl)ethenone (31). 42 mg, 45%
General Procedure A (39 mg, 42% General Procedure B), white
solid. Melting point: 71.2−72.5 °C (PE/EA 20:1 (v/v)). This
compound is known, and the data reported here are consistent with
the literature.33 1H NMR (400 MHz, CDCl3) δ 7.98 (d, J = 2.1 Hz,
1H), 7.86 (dd, J = 8.6, 2.1 Hz, 1H), 6.96 (d, J = 8.6 Hz, 1H), 3.96 (s,
3H), 2.55 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 195.7, 158.7,
130.9, 130.6, 128.7, 122.8, 111.2, 56.3, 26.3.
1-(4-Methoxy-3-methylphenyl)ethenone (32). 46 mg, 56%
General Procedure A (41 mg, 50% General Procedure B), colorless
oil (PE/EA 20:1 (v/v)). This compound is known, and the data
reported here are consistent with the literature.33 1H NMR (400
MHz, CDCl3) δ 7.80 (d, J = 8.5 Hz, 1H), 7.75 (s, 1H), 6.82 (d, J =
8.5 Hz, 1H), 3.87 (s, 3H), 2.53 (s, 3H), 2.23 (s, 3H). 13C{1H} NMR
(100 MHz, CDCl3) δ 197.1, 161.7, 130.8, 129.6, 128.4, 126.6, 109.0,
55.4, 26.3, 16.2.
1-(4-Chloro-3-nitrophenyl)ethenone (33). 54 mg, 54% General
Procedure A (49 mg, 49% General Procedure B), white solid. Melting
1
point: 105.6−107.0 °C (PE/EA 20:1 (v/v)). H NMR (400 MHz,
CDCl3) δ 8.40 (s, 1H), 8.07 (d, J = 8.3 Hz, 1H), 7.67 (d, J = 8.4 Hz,
1H), 2.64 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 194.5, 148.1,
136.3, 132.4, 132.1, 131.7, 125.3, 26.5. HRMS (EI): m/z [M]+ Calcd
+
for C8H6ClNO3 : 199.0031, 201.0002, found: 199.0031, 201.0004.
1-(4-Methyl-3-nitrophenyl)ethenone (34). 43 mg, 48% General
Procedure A (36 mg, 40% General Procedure B), yellow solid.
Melting point: 61.5−63.4 °C (PE/EA 20:1 (v/v)). This compound is
known, and the data reported here are consistent with the literature.34
1H NMR (400 MHz, CDCl3) δ 8.49 (s, 1H), 8.06 (dd, J = 8.0, 1.4 Hz,
1H), 7.46 (d, J = 8.0 Hz, 1H), 2.65 (s, 3H), 2.63 (s, 3H). 13C{1H}
NMR (100 MHz, CDCl3) δ 195.5, 149.2, 138.5, 136.0, 133.3, 131.9,
124.5, 26.5, 20.5.
F
J. Org. Chem. XXXX, XXX, XXX−XXX