Phosphorus tribromide → (4-Bromomethyl-2-methyl-benzyloxy)-tert-butyl-diphenyl-silane

HRID 390399Notes

Reaction equation

HRID 390399 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]O)=[CH:22][C:21]=1[CH3:28])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:30]>C(Cl)Cl>[Br:30][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:21]([CH3:28])[CH:22]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 67087256[4-[(Tert-butyl(diphenyl)silyl)oxymethyl]-3-methyl-phenyl]methanol

Product 1

HCID 58230580(4-Bromomethyl-2-methyl-benzyloxy)-tert-butyl-diphenyl-silaneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of [4-[(tert-butyl(diphenyl)silyl)oxymethyl]-3-methyl-phenyl]methanol (0.3 g, 0.76 mmol) in DCM (30 mL) is added phosphorus tribromide (0.072 mL, 0.76 mmol) at 0° C. and the reaction mixture is stirred for 1 hour. The reaction mixture is diluted with dichloromethane (50 mL), washed with aqueous sodium bicarbonate solution, dried over magnesium sulphate, and concentrated under vacuum to give the title compound as a light yellow liquid (0.3 g, crude). ESI/MS m/z 438.1 (M+H)+.

Workup

  1. washwashed with aqueous sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c28f992fa71246a09c9cec71d78e2de0
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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