Imidazole → Tert-butyl-(3,5-difluoro-phenoxy)-diphenyl-silane

HRID 1247362Notes

Reaction equation

HRID 1247362 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.[C:10]([Si:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)Cl)([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>C(Cl)Cl>[C:10]([Si:14]([O:9][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 759283,5-DifluorophenolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 21905446Tert-butyl-(3,5-difluoro-phenoxy)-diphenyl-silaneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well stirred ice cooled solution of 3,5-difluorophenol (30.0 g) in CH2Cl2 (500 ml) under N2 were added tert-butyldiphenylchlorosilane (63.4 g) and imidazole (17.3 g). The reaction mixture was stirred 15 min before removing the cooling bath. After 3.5 h the reaction was stopped by washing 1 N HCl sol. (2×300 ml and 1×200 ml), sat. aq. Na2CO3 sol. (200 ml) and brine (200 ml). The aqueous layers were extracted with more CH2Cl2 (200 ml). After drying (MgSO4) the solvent was evaporated to obtain 84.8 g (100%) of tert-butyl-(3,5-difluoro-phenoxy)-diphenyl-silane. Colorless oil. MS 368.1 (M+).

Workup

  1. custombefore removing the cooling bath
  2. waitAfter 3.5 h the reaction was stopped
  3. washby washing 1 N HCl sol. (2×300 ml and 1×200 ml), sat. aq. Na2CO3 sol. (200 ml) and brine (200 ml)
  4. extractionThe aqueous layers were extracted with more CH2Cl2 (200 ml)
  5. dry with materialAfter drying (MgSO4) the solvent
  6. customwas evaporated

Sources & evidence

ORD record
ord-88834406655e46eebda91a4b9c8ab36c
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

Loading…