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Imidazole → 2-Bromo-5-chloro-3-t-butyldimethylsilyloxy-methylbenzene

HRID 1081886
Notes
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Reaction equation

HRID 1081886 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4]O.N1C=CN=C1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].CN(C=[O:28])C>CCOCC>[Br:1][C:2]1[C:9]([O:28][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21])=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228Dimethylformamide2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 23363134(2-Bromo-5-chlorophenyl)methanol

Product 1

HCID 540356052-Bromo-5-chloro-3-t-butyldimethylsilyloxy-methylbenzene

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Procedure

To the solution of 2-bromo-5-chlorobenzylalcohol (10 g) from Example 73 and imidazole (3.23 g) in dry DMF (50ml) was added dropwise t-butyl chloro dimethylsilane in dry DMF (10 ml) for 20 minutes at -0° C. After addition, the mixture was stirred for 30 minutes at room temperature. The mixture was diluted with ether, and washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate.

Workup

  1. additionAfter addition
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-88b7559467854c518a0df0ac0ab495bd
Source dataset
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05587392

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes