Imidazole → (3-Bromo-2-methylphenethoxy)(tert-butyl)dimethylsilane

HRID 446399Notes

Reaction equation

HRID 446399 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][CH2:9][O:10][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 581685412-(3-Bromo-2-methylphenyl)ethan-1-ol2×

Product 1

HCID 58168609(3-Bromo-2-methylphenethoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(3-bromo-2-methylphenyl)ethanol [Aromatic Intermediate 22, step b] (1.67 g) and imidazole (1.60 g) in DMF (20 mL) was cooled in ice-water, treated with tert-butyldimethylchlorosilane (1.31 g), then removed from the cooling bath and stirred at room temperature overnight. The solution was poured into water and extracted twice with diethyl ether. The combined organic extracts were washed twice with water, once with brine, then dried over anhydrous magnesium sulphate and purified by flash chromatography on silica eluted with 10% dichloromethane in isohexane to afford the subtitled compound as a colourless oil. Yield 2.06 g.

Workup

  1. customremoved from the cooling bath
  2. additionThe solution was poured into water
  3. extractionextracted twice with diethyl ether
  4. washThe combined organic extracts were washed twice with water, once with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. custompurified by flash chromatography on silica
  7. washeluted with 10% dichloromethane in isohexane

Sources & evidence

ORD record
ord-77e62000072d4ae1bf6ef4f4a4f5ea0c
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

Loading…