Chlorotrimethylsilane → 4-bromobenzyl trimethylsilyl ether

HRID 380278Notes

Reaction equation

HRID 380278 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH3:1][Si:2]([O:12][CH2:11][C:10]1[CH:13]=[CH:14][C:7]([Br:6])=[CH:8][CH:9]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 701194-Bromobenzyl alcohol

Product 1

HCID 5982014-bromobenzyl trimethylsilyl ether

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyl chloride (1.9 ml, 15 mmol) was added dropwise to a stirred solution of 4-bromobenzyl alcohol (2.0 g, 11 mmol) in toluene (25 ml) and pyridine (2 ml) at 0° C. The stirred mixture was heated to ambient temperature during 3 hours. The reaction mixture was filtered and the organic solution evaporated to yield pure 4-bromobenzyl trimethylsilyl ether. The silyl ether can be further purified by distillation (b.p. 73° C., 0.1 mm Hg). Yield after distillation: 1.49 g (50%)

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe organic solution evaporated

Sources & evidence

ORD record
ord-8028f56db1e74f5dbeab333376a74bcf
Source dataset
uspto-grants-2001_10
Patent number
US06303101B1

Reaction notes

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