Carbon tetrabromide → [2-(Bromomethyl)phenoxy](tert-butyl)dimethylsilane

HRID 481007Notes

Reaction equation

HRID 481007 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[Br:18][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10966587Benzenemethanol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

Product 1

HCID 13594450[2-(Bromomethyl)phenoxy](tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

[2-(Bromomethyl)phenoxy](tert-butyl)dimethylsilane was prepared according to the literature procedure (J. Chem. Soc. Perkin Trans.1; 1988; 1417). To a solution of (2-([tert-butyl(dimethyl)silyl]oxy}phenyl)methanol (9.9 g/41.5 mmol) in acetonitrile (200 ml) was added carbon tetrabromide (14.5 g/43.6 mmol), triphenylphosphine (11.4 g/43.6 mmol) successively at 0° C., and then the resulting solution was stirred at room temperature for 16 hours. The solvent was evaporated. The residue was purified by column chromatography (SiO2, 200-350 mesh/hexane:ethyl acetate=100:1-20:1-10:1) to afford a colorless oil (12.0 g/96%).

Workup

  1. customThe solvent was evaporated
  2. customThe residue was purified by column chromatography (SiO2, 200-350 mesh/hexane:ethyl acetate=100:1-20:1-10:1)
  3. customto afford a colorless oil (12.0 g/96%)

Sources & evidence

ORD record
ord-aaaf493d97cc4547a6862f289fca25fe
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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