Imidazole → Tert-butyl-(2,4-difluoro-phenoxy)-diphenyl-silane

HRID 1247378Notes

Reaction equation

HRID 1247378 reaction equation
[C:1]([Si:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)Cl)([CH3:4])([CH3:3])[CH3:2].[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[OH:27].N1C=CN=C1>C(Cl)Cl>[C:1]([Si:5]([O:27][C:21]1[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=1[F:19])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 1230512,4-Difluorophenol

Product 1

HCID 21904942Tert-butyl-(2,4-difluoro-phenoxy)-diphenyl-silaneYield 104.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butydiphenylchlorosilane (76.8 g) was added over 30 min to a cooled (0° C.) solution of 2,4-difluorophenol (34.6 g) and imidazole (19.9 G) in CH2Cl2 (400 ml). The cooling bath was removed and the reaction mixture was stirred 2 h at rt before washing it with H2O (400 ml), 5% aq. NaHCO3 (300 ml) and brine. The aqueous layers were extracted with two more portions of CH2Cl2 (150 ml). The combined organic layers were dried (Na2SO4) and the solvent was evaporated to obtain 102 g (99%) of tert-butyl-(2,4-difluoro-phenoxy)-diphenyl-silane. Colorless liquid.

Workup

  1. customThe cooling bath was removed
  2. washbefore washing it with H2O (400 ml), 5% aq. NaHCO3 (300 ml) and brine
  3. extractionThe aqueous layers were extracted with two more portions of CH2Cl2 (150 ml)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0749d5a2390c44f9a78ac31f450fb3dc
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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