Imidazole → 1-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene

HRID 1731801Notes

Reaction equation

HRID 1731801 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].N1C=CN=C1.[CH3:15][Si:16]([CH3:22])([C:18]([CH3:21])([CH3:20])[CH3:19])Cl.CN(C)C=O>O>[CH3:15][Si:16]([O:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[CH:3]=1)([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 851413-Bromobenzyl alcohol

Product 1

HCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzeneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g 3-bromobenzyl alcohol, imidazole (3.64 g), dimethyl-t-butylchlorosilane (4.02 g) and N,N-dimethylformamide (25 ml) was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted three times with ether. The combined organic extract was washed with water, brine and dried. Evaporation gave the product as a colorless oil (6.83 g, 85% yield) which was used without further purification.

Workup

  1. extractionextracted three times with ether
  2. extractionThe combined organic extract
  3. washwas washed with water, brine
  4. customdried
  5. customEvaporation

Sources & evidence

ORD record
ord-434f0b580b4c448b8224c208903132d6
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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