Imidazole → (3-Bromophenoxy)(tert-butyl)dimethylsilane

HRID 2249462Notes

Reaction equation

HRID 2249462 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([Si:13](Cl)([CH3:15])[CH3:14])([CH3:12])([CH3:11])[CH3:10].N1C=CN=C1.O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][Si:13]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 115633-BromophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11254705(3-Bromophenoxy)(tert-butyl)dimethylsilaneYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromophenol (400 g, 2.31 mol), tert-butylchlorodimethylsilane (391 g, 2.54 mol), and imidazole (346 g, 5.08 mol) in 5000 mL of dichloromethane was stirred overnight at room temperature. The reaction solution was poured into 2000 mL of water and the layers were separated. The organic layer was washed with 1N aqueous sodium hydroxide solution (3×1500 mL) and water (2×1500 mL) before passing through a pad of silica gel (400 g, silica 60, 230-400 mesh). The silica gel was washed with dichloromethane (2×500 mL), the filtrates were combined and the solvent removed under reduced pressure to give 669 g (98.4%) of 3-bromophenoxy-tert-butyldimethylsilane as a clear pale yellow liquid. 1H NMR (CDCl3, 300 MHz): δ7.1 (m, 2H); 7.0 (br s, 1H); 6.75 (m,1H); 1.0 (s, 9H); 0.2 (s, 6H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with 1N aqueous sodium hydroxide solution (3×1500 mL) and water (2×1500 mL)
  3. washThe silica gel was washed with dichloromethane (2×500 mL)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a44cecd46b3c45fab2212b65f1e296a2
Source dataset
uspto-grants-2008_01
Patent number
US07314880B2

Reaction notes

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