Imidazole → 1-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene

HRID 1757437Notes

Reaction equation

HRID 1757437 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1.O>C(Cl)Cl>[Si:10]([O:6][CH2:5][C:4]1[CH:3]=[C:2]([Br:1])[CH:9]=[CH:8][CH:7]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 851413-Bromobenzyl alcohol

Product 1

HCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzeneYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromobenzyl alcohol (5.00 g, 26.7 mmol) in freshly drieddimethylformamide (10 mL) was added t-butyldimethylsilyl chloride (5.13 g, 33 mmol) and imidazole (4.56 g, 67 mmol). The resulting solution was stirred overnight at ambient temperature. The reaction mixture was poured into water and extracted (3x, 50 mL 1:1 ether:hexanes). The combined organic layers were washed (2x, brine), dried over MgSO4, filtered, and concentrated in vacuo to give a colorless oil which was passed througha short silica gel plug using 10% methylene chloride:hexanes to give pure 3-(t-butyldimethylsilyloxymethyl)bromobenzene (7.9 g, 98%). 1H NMR (300 MHz, CDCl3) δ 7.47 (1H, br s), 7.37 (1H, dt, J =7, 1 Hz), 7.16-7.25 (2H, m), 4.24 (2H, s), 0.94 (9H, s), 0.11 (6H, s). MS m/e 318/320(M+NH4)+.

Workup

  1. extractionextracted (3x, 50 mL 1:1 ether:hexanes)
  2. washThe combined organic layers were washed (2x, brine)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a colorless oil which

Sources & evidence

ORD record
ord-94cfe40066b04d62a44ba142a762167a
Source dataset
uspto-grants-1995_08
Patent number
US05446055

Reaction notes

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