Water → HCID 18434147, compound

HRID 2306470Notes

Reaction equation

[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].C[Si](C)(C)[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[O:19])=[CH:14][CH:13]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]([C:15]2[CH:16]=[CH:17][C:12]([OH:11])=[CH:13][CH:14]=2)([OH:19])[C:2]([F:4])([F:3])[F:1])=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Ed) 4 ml of trifluoromethyltrimethylsilane are added to a a solution of 3.1 g of 4-trimethylsilyloxyphenyl-(4-bromo-phenyl)-methanone in 60 ml of THF at 0° C. under argon. After stirring at 0° C. for 30 min. 69.3 ml of 1M tetrabutylammonium fluoride solution in THF are added dropwise. The reaction mixture is warmed to room temperature and stirred, subsequently treated with 40 ml of water, again stirred and then extracted with methylene chloride. The extracts are washed with saturated sodium chloride solution, dried and evaporated. The crude product is purified over silica gel with toluene/acetone (98:2) as the eluent. 3.0 g of (RS)4-[1-(4-bromo-phenyl)-2,2,2-trifluoro-1-hydroxyl-ethyl]-phenol, MS: m/e 290 (M-CO, 1Br), are obtained.

Workup

temperatureThe reaction mixture is warmed to room temperature
stirringstirred
stirringagain stirred
extractionextracted with methylene chloride
washThe extracts are washed with saturated sodium chloride solution
customdried
customevaporated
customThe crude product is purified over silica gel with toluene/acetone (98:2) as the eluent

Sources & evidence

ORD record: ord-b3b7c1802beb405bbda7f4e368949de8
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441177B1

Reaction notes

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