Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

HRID 1731800Notes

Reaction equation

HRID 1731800 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.N1C=CN=C1.[CH3:15][Si:16](Cl)([CH3:21])[C:17]([CH3:20])([CH3:19])[CH3:18].CN(C)C=O>O>[CH3:15][Si:16]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)([CH3:21])[C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 108595834-Bromobenzyloxy-tert-butyldimethylsilaneYield 99.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 18.7 g 4-bromobenzyl alcohol, imidazole (13.6 g), dimethyl-t-butylsilyl chloride (15 g) and N,N-dimethylformamide (100 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 extracts was washed with water, brine and dried. Evaporation gave the product as a colorless oil (29.8 g, 99% yield) which was used without further purification. NMR (CDCl3, 250 MHz): 7.55 (d, 2H, J=9 Hz), 7.25 (d, 2H, J=9 Hz), 4.7 (s, 2H), 0.9 (s, 9H), 0.0 (s, 6H).

Workup

  1. extractionextracted three times with ether
  2. washThe combined organic extracts was washed with water, brine
  3. customdried
  4. customEvaporation

Sources & evidence

ORD record
ord-9612778d09a340528f7fc6bf561f36b4
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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