Imidazole → 1-Bromo-4-(tert-butyldiphenylsilyloxymethyl)-3-methylbenzene

HRID 584212Notes

Reaction equation

HRID 584212 reaction equation
[C:1]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][OH:30])=[C:27]([CH3:33])[CH:26]=1>>[Br:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][O:30][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:27]([CH3:33])[CH:26]=1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 22280088(4-Bromo-2-methylphenyl)methanol

Product 1

HCID 223426891-Bromo-4-(tert-butyldiphenylsilyloxymethyl)-3-methylbenzeneYield 98.2%

Procedure

Tert-butylchlorodiphenylsilane (13.06 g) and imidazole (9.7 g) were added to a solution of 4-bromo-2-methylbenzyl alcohol (9.55 g) in N,N-dimethylfocmamide (80 ml) at 5° C. and the mixture was allowed to warm to room temperature, and stirred for 18 hours. The mixture was extracted with ethyl acetate and the extract was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give 1-bromo-4-(tert-butyldiphenylsilyloxymethyl)-3-methylbenzene (20.5 g) as a colorless oil.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2384f4a54d448f3aadee38ca3dfa9cf
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

Loading…