Imidazole → 1-(Tert-butyldimethylsiloxy)-2-methyl-3-(4-bromophenyl)propane

HRID 361437Notes

Reaction equation

HRID 361437 reaction equation
N1C=CN=C1.[CH3:6][CH:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)[CH2:8][OH:9].[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[O:9]([CH2:8][CH:7]([CH3:6])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=1)[Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 217141993-(4-Bromophenyl)-2-methylpropan-1-ol

Product 1

HCID 211863601-(Tert-butyldimethylsiloxy)-2-methyl-3-(4-bromophenyl)propaneYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of imidazole (27.2 g) in DMF (100 ml) was added to a stirred solution of 2-methyl-3-(4-bromophenyl)propanol (37.4 g) and tert-butyldimethylsilyl chloride (28.9 g) in dry DMF (100 ml) at 0° C. The reaction mixture was allowed to stir, warming to ambient temperature, over 21 hours and was then poured onto ice (500 g). The reaction mixture was extracted with diethyl ether (3×500 ml), the combined organic layers were dried (MgSO4) and the solvent was evaporated to give 1-(tert-butyldimethylsiloxy)-2-methyl-3-(4-bromophenyl)propane as a yellow oil (53.3 g), mass spectrum (+ve CI): 343 (M+H)+.

Workup

  1. additionwas then poured onto ice (500 g)
  2. extractionThe reaction mixture was extracted with diethyl ether (3×500 ml)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-43ab19153e294b5d8afd462d1b9262e9
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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