Please do not adjust margins
Organic & Biomolecular Chemistry
Page 6 of 9
DOI: 10.1039/C6OB00532B
ARTICLE
Journal Name
3H); 13C NMR (100 MHz, CDCl3) δ 138.2, 135.5, 131.3, 128.8,
127.1, 126.9, 58.1, 24.7, 19.4.
1-Chloro-4-(2-iodo-1-(2,2,2-trifluoroethoxy)ethyl)benzene
(3d): Rf 0.4 (in hexane); colourless liquid; yield 52% (138
=
9-(1-Azido-2-iodoethyl)-9H-carbazole (2k): Rf = 0.33 (in mg); 19F NMR (376.3 MHz, CDCl3) δ -73.7; H NMR (400 MHz,
hexane); semisolid, yield 68% (127 mg); 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J = 8 Hz, 2H), 7.27 (d, J = 8 Hz, 2H), 4.57-4.54
CDCl3) δ 8.11 (d, J = 7.8 Hz, 2H), 7.61 (d, J = 8.3 Hz, 2H), 7.51 – (m, 1H), 3.77-3.70 (m, 2H), 3.41-3.37 (m, 1H), 3.32-3.28 (m,
7.47 (m, 2H), 7.33 (t, J = 7.5 Hz, 2H), 6.44 (dd, J = 7.8, 6.7 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 136.9, 135.1, 129.3, 128.1,
1H), 3.80 (dd, J = 10.7, 7.9 Hz, 1H), 3.68 (dd, J = 10.7, 6.7 Hz, 123.7 (q, 1JC,F = 277 Hz), 82.8, 66.7 (q, 2JC,F = 35 Hz), 8.3; HR-MS
1H); 13C NMR (100 MHz, CDCl3) δ 138.8, 126.4, 124.2, 120.8, (ESI-TOF): m/z = 386.9256, calculated for (M+Na+) 386.9231.
1
120.8, 110.3, 73.0, 2.9.
2-(2-Iodo-1-(2,2,2-trifluoroethoxy)ethyl)-1,3,5-
1-(1-Azido-2-iodoethyl)-4-chlorobenzene (2l):76 Rf = 0.25 (in trimethylbenzene (3e): Rf = 0.7 (in hexane); colourless liquid;
hexane); colorless oil; yield 92% (235 mg); H NMR (400 MHz, yield 68% (86 mg); 19F NMR (376.3 MHz, CDCl3) δ -73.5; 1H
1
CDCl3) δ 7.40 (d, J = 8.5 Hz, 2H), 7.28 (d, J = 8.5 Hz, 2H), 4.71 (t, NMR (400 MHz, CDCl3) δ 6.87 (s, 2H), 5.11-5.08 (m, 1H), 3.75-
J = 6.9 Hz, 1H), 3.41 – 3.34 (m, 2H); 13C NMR (100 MHz, CDCl3) 3.62 (m, 3H), 3.40-3.36 (m, 1H), 2.38 (s, 6H), 2.28 (s, 3H); 13C
1
NMR (100 MHz, CDCl3) δ 138.3, 136.9, 130.4, 124.0 (q, JC,F
δ 136.5, 135.1, 129.4, 128.2, 66.4, 7.9.
=
1-(1-Azido-2-iodoethyl)-4-methylbenzene (2m):45 Rf = 0.33 277 Hz), 80.8, 66.4 (q, 2JC,F = 34 Hz), 20.9, 20.4, 5.7; HR-MS (ESI-
(in hexane); colorless oil; yield 75% (163 mg); 1H NMR (400 TOF): m/z = 395.0116, calculated for (M+Na+) 395.0090.
MHz, CDCl3) δ 7.23-7.21 (br, 4H), 4.70 (t, J = 7.0 Hz, 1H), 3.39
1-(2-Iodo-1-(2,2,2-trifluoroethoxy)ethyl)-4-
(d, J = 7.1 Hz, 2H), 2.38 (s, 3H); 13C NMR (100 MHz, CDCl3) δ isopropylbenzene (3f): Rf = 0.6 (in hexane); colourless liquid;
139.0, 134.9, 129.8, 126.6, 67.0, 21.3, 8.4.
yield 53% (142 mg); 19F NMR (376.3 MHz, CDCl3) δ -74.2; 1H
(2-Azido-1-iodopropan-2-yl)benzene (2n): Rf
1
=
0.32 (in NMR (400 MHz, CDCl3) δ 7.22-7.16 (m, 4H), 4.97-4.94 (m, 1H),
hexane); colorless oil; yield 78% (172 mg); H NMR (400 MHz, 3.97-3.90 (m, 4H), 2.98 (d, J = 4, 2H), 2.95-2.88 (m, 1H), 1.27
CDCl3) δ 7.46 – 7.33 (m, 5H), 3.50 (dd, J = 14, 12 Hz, 2H), 1.90 (d, J = 8, 6H); 13C NMR (100 MHz, CDCl3) δ 147.8, 132.3, 129.4,
(s, 3H); 13C NMR (100 MHz, CDCl3) δ 140.8, 128.9, 128.4, 125.7, 126.8, 123.8 (q, JC,F = 276 Hz), 104.1, 62.8 (q, JC,F = 35 Hz),
1
2
65.2, 25.3, 17.9.
(1-Azido-2-iodoethane-1,2-diyl)dibenzene (2o):16 Rf = 0.30
39.2, 33.9, 24.1.
1-(2-Iodo-1-(2,2,2-trifluoroethoxy)ethyl)-4-methylbenzene
o
(in hexane); white solid; yield 63% (122 mg); mp 99 – 103 C; (3g): Rf
= 0.7 (in hexane); colourless liquid; yield 70% (120
1
1
E:Z = 1:1, H NMR (400 MHz, CDCl3) δ 7.45 (d, J = 6.7 Hz, 2H), mg); 19F NMR (376.3 MHz, CDCl3) δ -74.2; H NMR (400 MHz,
7.42 – 7.36 (m, 3H), 7.36 – 7.27 (m, 5H), 7.25 – 7.20 (m, 5H), CDCl3) δ 7.69 (d, J = 4, 1H), 7.17 (d, J = 8, 2H), 7.12-7.09 (m,
7.20 – 7.08 (m, 5H), 5.21 (dd, J = 15.4, 9.4 Hz, 2H), 5.11 (d, J = 1H), 4.89 (t, J1 = J2 = 4, 1H), 3.99-3.85 (M, 4H), 2.90 (d, J = 8,
9.2 Hz, 1H), 4.94 (d, J = 9.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) 2H), 2.41 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 140.3, 139.8,
δ 140.3, 140.2, 137.8, 136.4, 129.2, 128.8, 128.8, 128.7, 128.6, 134.2, 129.8, 129.4, 123.7 (q, 1JC,F = 276 Hz), 103.8, 101.2, 62.9
128.6, 128.4, 128.4, 127.8, 127.4, 72.9, 72.0, 36.8, 34.5.
(2-Iodo-1-(2,2,2-trifluoroethoxy)ethyl)benzene (3a):77 Rf
(q, 2JC,F = 35 Hz), 38.5, 27.8.
=
2-Iodo-1-(2,2,2-trifluoroethoxy)-2,3-dihydro-1H-indene
0.6 (in hexane); colourless liquid; yield 75% (120 mg); 19F NMR (3h): Rf
= 0.4 (in hexane); colourless liquid; yield 52% (154
1
(376.3 MHz, CDCl3) δ -73.76; H NMR (400 MHz, CDCl3) δ 7.43- mg); 19F NMR (376.3 MHz, CDCl3) δ -74.3; d.r. ˃ 19 : 1; 1H NMR
7.36 (m, 3H), 7.35-7.32 (m, 2H), 4.59 (dd, J1 = J2 = 8 Hz, 1H), (400 MHz, CDCl3) δ 7.48-7.41 (m, 1H), 7.37-7.27 (m, 3H), 5.34
3.82-3.67 (m, 2H), 3.45-3.40 (m, 2H), 3.36-3.32 (m, 2H); 13C (d, J = 8, 1H), 4.46-4.42 (m, 1H), 4.22-4.09 (m, 2H), 3.75-3.69
1
NMR (100 MHz, CDCl3) δ 138.3, 129.2, 129.1, 123.9 (q, JC,F
=
(m, 1H), 3.34-3.28 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 141.5,
278 Hz), 83.6, 66.6 (q, 2JC,F = 35 Hz), 8.7; HR-MS (ESI-TOF): m/z 139.2, 129.7, 127.6, 125.1, 124.8, 124.0 (q, 1JC,F = 278 Hz), 93.5,
= 352.9646, calculated for (M+Na+) 352.9621.
4-(2-Iodo-1-(2,2,2-trifluoroethoxy)ethyl)-1,1'-biphenyl (3b): 364.9644, calculated for (M+Na+): 364.9621.
Rf = 0.5 (in hexane); colourless liquid; yield 57% (77 mg); 19F
1-(2-Iodo-1-(2,2,2-trifluoroethoxy)ethyl)-4-
67.4 (q, JC,F = 34 Hz), 43.3, 24.9; HR-MS (ESI-TOF) m/z =
2
NMR (376.3 MHz, CDCl3) δ -73.69; 1H NMR (400 MHz, CDCl3) δ methoxybenzene (3i): Rf = 0.3 (hexane : ethyl acetate 19 :1);
7.64-7.59 (m, 4H), 7.48-7.45 (m, 2H), 7.41-7.38 (m, 3H), 4.65 colourless liquid; yield 55% (88 mg); 19F NMR (376.3 MHz,
(dd, J1 = J2 = 8 Hz, 1H), 3.87-3.71 (m, 2H), 3.48-3.44 (m, 1H), CDCl3) δ -74.2; 1H NMR (400 MHz, CDCl3) δ 7.65 (d, J = 2.4, 1H),
3.40-3.66 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 142.2, 140.4, 7.18-7.16 (m, 1H), 6.76 (d, J = 8, 1H), 4.87 (t, J1 = J2 = 4, 1H),
1
137.2, 129.0, 127.9, 127.8, 127.3, 127.2, 123.9 (q, JC,F = 277 3.96-3.87 (m, 4H), 3.86 (s, 3H), 2.88 (d, J = 4, 2H); 13C NMR (100
2
Hz), 83.3, 66.6 (q, JC,F = 35 Hz), 8.6; HR-MS (ESI-TOF): m/z = MHz, CDCl3) δ 157.4, 140.3, 130.6, 129.0, 123.7 (q, JC,F = 277
1
428.9962, calculated for (M+Na+) 428.9934.
Hz), 110.9, 103.9, 86.0, 62.9 (q, 2JC,F = 35 Hz), 56.5, 38.2.
(1-Iodo-2-(2,2,2-trifluoroethoxy)propan-2-yl)benzene (3c):
2-(2-Iodo-1-(2,2,2-trifluoroethoxy)ethyl)isoindoline-1,3-
Rf = 0.6 (in hexane); colourless liquid; yield 48% (70 mg); 19F dione (3j): Rf = 0.3 (hexane : ethyl acetate 19 :1); colourless
1
NMR (376.3 MHz, CDCl3) δ -73.8; H NMR (400 MHz, CDCl3) δ liquid; yield 88% (122 mg); 19F NMR (376.3 MHz, CDCl3) δ -74.2;
7.42-7.34 (m, 5H), 3.67-3.60 (m, 1H), 3.59-3.53 (m, 2H), 3.47- 1H NMR (400 MHz, CDCl3) δ 7.93-7.90 (m, 2H), 7.82-7.79 (m,
3.44 (m, 1H), 1.79 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 140.1, 2H), 5.69-5.65 (m, 1H), 4.14-4.08 (m, 1H), 4.06-3.87 (m, 2H),
128.9, 128.6, 126.4, 124.0 (q, 1JC,F = 277 Hz), 78.5, 62.2 (q, 2JC,F
=
3.82-3.78 (m, 1H); 13C NMR (100 MHz, CDCl3) δ 167.3, 134.9,
1
131.3, 124.2, 123.4 (q, JC,F = 277 Hz), 82.9, 67.1 (q, JC,F = 35
2
34 Hz), 23.85, 18.0.
Hz), 1.2.
6 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins