Imidazole → {[(5-Bromo-2,3-dichlorophenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane

HRID 337584Notes

Reaction equation

HRID 337584 reaction equation
CN(C=O)C.[Br:6][C:7]1[CH:8]=[C:9]([Cl:16])[C:10]([Cl:15])=[C:11]([CH2:13][OH:14])[CH:12]=1.Cl[Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1>CCOCC>[Br:6][C:7]1[CH:8]=[C:9]([Cl:16])[C:10]([Cl:15])=[C:11]([CH2:13][O:14][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:12]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 66896066(5-Bromo-2,3-dichlorophenyl)methanol

Product 1

HCID 66896768{[(5-Bromo-2,3-dichlorophenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a DMF (0.34 M) solution of (5-bromo-2,3-dichlorophenyl)methanol (1 eq.) from the previous step was added chloro(1,1-dimethylethyl)dimethylsilane (1.1 eq.) and imidazole (1.5 eq.). The resulting yellow solution was stirred at RT for 16 h. The reaction mixture was then diluted with ether and washed sequentially with 10% aq. HCl, water and brine. The ether extract was dried Na2SO4, filtered and the filtrate concentrated in vacuo to afford the crude title compound as a colorless oil.

Workup

  1. washwashed sequentially with 10% aq. HCl, water and brine
  2. extractionThe ether extract
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e936479dd3e4466a93cfc0f4cd6fa63d
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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