Carbon tetrabromide → 3-Tert-butyldimethylsilyloxymethylbenzyl bromide

HRID 1351093Notes

Reaction equation

HRID 1351093 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:16]O)[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:18]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[CH2:16][Br:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10658493(3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanol

Product 1

HCID 210978413-Tert-butyldimethylsilyloxymethylbenzyl bromideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-tert-butyldimethylsilyloxymethylphenyl)methanol (528 mg) and tetrabromomethane (694 mg) in dichloromethane (10 mL) was added triphenylphosphine (549 mg) at room temperature, and the mixture was stirred for 2 hours. The reaction mixture was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give the title compound (660 mg).

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-30cbfc922b184fd3ad42bbc4f099c149
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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