Imidazole → 4-(Tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxy)-fluorobenzene

HRID 1266711Notes

Reaction equation

HRID 1266711 reaction equation
[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][C:7]1[CH:8]=[CH:9][C:10]([F:14])=[C:11]([OH:13])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[Si:17](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C=CN=C1>CN(C=O)C>[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][C:7]1[CH:8]=[CH:9][C:10]([F:14])=[C:11]([O:13][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 138616985-[(Tert-butyldimethylsilyl)oxy]-2-fluorophenol

Product 1

HCID 185518264-(Tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxy)-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 53.0 g 5-(tert-butyl-dimethyl-silanyloxy)-2-fluoro-phenol (M. Kawase, A. K. Sinhababu, R. T. Borchardt, Chem. Pharm. Bull. (1990),38, 2939) in 120 ml DMF was cooled to 0° C. Within 15 min 61.6 ml tert-butyldiphenylsilyl chloride were added. Then 16.4 g imidazole were added portionwise. The suspension was stirred overnight, then quenched with 150 ml H2O at 0° C. The crude product was isolated by extraction with hexanes and purified by chromatography on silica gel (hexanes) to yield 88.9 g of 4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxy)-fluorobenzene as colorless liquid.

Workup

  1. customquenched with 150 ml H2O at 0° C
  2. customThe crude product was isolated by extraction with hexanes
  3. custompurified by chromatography on silica gel (hexanes)

Sources & evidence

ORD record
ord-e7e108a5af7847e4bbbee199cb2f5c66
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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