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

HRID 1490063Notes

Reaction equation

HRID 1490063 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([Si:13](Cl)([CH3:15])[CH3:14])([CH3:12])([CH3:11])[CH3:10].N1C=CN=C1>CN(C)C=O>[Si:13]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 115633-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11254705(3-Bromophenoxy)(tert-butyl)dimethylsilaneYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1400 g (8.1 mol) of 3-bromophenol, 1218 g (8.1 mol) of tert-butylchlorodimethylsilane and 1376 g (20.2 mol) of imidazole in 1600 mL of N,N-dimethylformamide was stirred at room temperature under nitrogen for 18 hours. The reaction mixture was poured into pH 8 aqueous buffer solution and extracted with diethyl ether. The ether extracts were washed with water and brine, dried over sodium sulfate, and the solvent was evaporated under vacuum to give 2314 g of crude 3-bromophenyl tert-butyldimethylsilyl ether as an orange oil. NMR (CDCl3, 200 MHz) δ: 0.2 (s, 6H); 0.95 (s, 9H); 6.8 (m, 1H); 7.0-7.1 (m, 3H).

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-e23e1a3042e4404bb1094d16416608a4
Source dataset
uspto-grants-1997_10
Patent number
US05681830

Reaction notes

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