Water → (5-Bromo-2-chlorobenzyloxy)(tert-butyl)diphenylsilane

HRID 221150Notes

Reaction equation

HRID 221150 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH2:7][OH:8].C(N(C(C)C)CC)(C)C.[C:20]([Si:24]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)Cl)([CH3:23])([CH3:22])[CH3:21].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH2:7][O:8][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 5074766(5-Bromo-2-chlorophenyl)methanol

Product 1

HCID 57516661(5-Bromo-2-chlorobenzyloxy)(tert-butyl)diphenylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-Bromo-2-chlorobenzylalcohol (5.15 g) in N,N-dimethylformamide (50 ml) was added diisopropylethylamine (19.8 ml) and tert-butyldiphenylchlorosilane (11.9 ml), and the mixture was stirred at room temperature for 2 days. Under ice-cooling, to the mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with successively with 0.4 M aqueous hydrochloric acid solution (twice), water, a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by an aminosilane-treated silica gel column chromatography (hexane) to give 5-bromo-2-chloro-1-(tert-butyldiphenylsiloxymethyl)benzene 77 (10.79 g) as colorless oil. APCI-Mass m/Z 476/478 (M+NH4).

Workup

  1. temperatureUnder ice-cooling, to the mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with successively with 0.4 M aqueous hydrochloric acid solution (twice), water
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine, and dried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by an aminosilane-
  7. additiontreated silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-025bb99909744c68b7fab9537bd0e935
Source dataset
uspto-grants-2012_06
Patent number
US08202984B2

Reaction notes

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