Benzonitrile, 4-bromo- → HCID 16110707, compound

HRID 605622Notes

Reaction equation

HRID 605622 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=2)=[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=CC(C#N)=CC=1>>[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]=[CH:29][C:30]([C:31]#[N:32])=[CH:33][CH:34]=3)=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 12162Benzonitrile, 4-bromo-HCID 16110681HCID 16110681, compoundHCID 670460482-(1-(Tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(tributylstannyl)oxazole

Product 1

HCID 16110707HCID 16110707, compoundYield 79%

Procedure

4-(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 (53 mg, 0.080 mmol) and 4-bromobenzonitrile following General Procedure A. Flash chromatography (5-10% EtOAc/hexanes) yielded the title compound as a clear oil (30 mg, 79%): 1H NMR (CDCl3, 500 MHz) δ 7.82-7.78 (m, 4H), 7.50 (s, 1H), 7.36-7.33 (m, 2H), 7.26-7.23 (m, 3H), 4.93 (t, 1H, J=5.5 Hz), 2.67 (t, 2H, J=7.5 Hz), 2.06-1.95 (m, 2H), 1.75-1.67 (m, 2H), 1.47-1.40 (m, 6H), 0.98 (s, 9H), 0.19 (s, 3H), 0.08 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 166.7, 149.7, 143.2, 133.2, 132.4, 128.8, 128.7, 126.0, 124.8, 124.8, 119.0, 112.0, 69.1, 36.8, 36.3, 31.8, 29.6, 28.3, 26.1, 25.5, 18.6, −4.5, −4.7.

Sources & evidence

ORD record
ord-e839c3af5d964de69691e281f43c8c41
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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