Imidazole → (3-Bromophenoxy)(tert-butyl)dimethylsilane

HRID 609817Notes

Reaction equation

HRID 609817 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1>CN(C)C=O>[Si:9]([O:8][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 115633-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11254705(3-Bromophenoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By the method of preparation 1, 3-bromophenol (5.0 g, 28.90 mmol) in dimethylformamide (20 mL) was treated with t-butyldimethylsilyl chloride (4.4 g, 28.9 mmol) and imidazole (3.9 g, 57.9 mmol) to provide, after chromatography (silica gel, hexanes), the desired product as a clear oil: 1H NMR d 0.22 (s, 6H), 1.00 (s, 9H), 6.78 (m, 1H), 7.02 (s, 1H), 7.10 (d, J=5.1 Hz, 2H); MS (FD) m/e 288 (M+); Anal. calc'd. for C12H19BrOSi: C, 50.17; H, 6.67. Found: C, 50.07; H, 6.45.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-a76ad791ce2944418d2c075dcdff7291
Source dataset
uspto-grants-1999_12
Patent number
US05998442

Reaction notes

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