3-Bromobenzonitrile → HCID 16110642, compound

HRID 605621Notes

Reaction equation

HRID 605621 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=2)[C:30]#[N:31])=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C(C)(C)C)(C)C.[Si](OC(C1OC([Sn](CCCC)(CCCC)CCCC)=CN=1)CCCCCCC1C=CC=CC=1)(C(C)(C)C)(C)C.BrC1C=C(C=CC=1)C#N>>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([C:22]2[O:23][C:24]([C:27]3[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=3)[C:30]#[N:31])=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 233813-BromobenzonitrileHCID 16110676HCID 16110676, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110642HCID 16110642, compoundYield 72%

Procedure

3-(2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)benzonitrile. The title compound was prepared from 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole (60 mg, 0.091 mmol) and 3-bromobenzonitrile following General Procedure A. Flash chromatography (2-5% EtOAc/hexanes) yielded the title compound as a clear oil (31 mg, 72%): 1H NMR (CDCl3, 600 MHz) δ 7.91 (s, 1H), 7.84 (d, 1H, J=7.8 Hz), 7.59 (d, 1H, J=7.8 Hz), 7.53 (t, 1H, J=7.8 Hz), 7.36 (s, 1H), 7.27-7.24 (m, 2H), 7.16-7.15 (m, 3H), 4.83 (t, 1H, J=6.0 Hz), 2.58 (t, 2H, J=7.8 Hz), 1.95-1.88 (m, 2H), 1.65-1.59 (m, 2H), 1.36-1.33 (m, 6H), 0.89 (s, 9H), 0.10 (s, 3H), −0.01 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ 166.8, 149.8, 143.6, 132.3, 130.7, 130.2, 129.2, 129.1, 128.9, 128.3, 126.5, 124.2, 119.1, 114.2, 69.5, 37.3, 36.8, 32.3, 30.0, 26.6, 26.6, 26.0, 19.1, −4.1, −4.2.

Sources & evidence

ORD record
ord-84eca55295ad4805bd3737eca4cc9dd9
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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