Water → alpha-(4-Fluorophenyl)-4-(trifluoromethyl)benzenemethanol

HRID 561418

반응식

HRID 561418 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.C([Li])CCC.[F:14][C:15]([F:25])([F:24])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][CH:17]=1.O>O1CCCC1.CCCCCC.ClCCl>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH:22]([C:19]2[CH:18]=[CH:17][C:16]([C:15]([F:14])([F:24])[F:25])=[CH:21][CH:20]=2)[OH:23])=[CH:3][CH:4]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 99931-Bromo-4-fluorobenzeneHCID 679964-(Trifluoromethyl)benzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 579773alpha-(4-Fluorophenyl)-4-(trifluoromethyl)benzenemethanol

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

1.00 g (5.71 mmol) of 4-bromofluorobenzene were dissolved in 10 ml of tetrahydrofuran at −78° C. Addition of 2.2 ml (6.86 mmol) of a 1.6N solution of n-butyllithium in hexane was followed by stirring for 15 min, and then 1.26 g (6.86 mmol) of trifluoro-p-tolualdehyde dissolved in 10 ml of tetrahydrofuran were added dropwise. The mixture was stirred at −78° C. for 1 h and then at RT for 1 h. The reaction solution was mixed with water and dichloromethane, and the phases were separated. The aqueous phase was extracted with dichloromethane, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the solvents were removed in vacuo. The crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient). 1.02 g (66% of theory) of the title compound were obtained.

후처리

  1. additionwere added dropwise
  2. stirringThe mixture was stirred at −78° C. for 1 h
  3. waitat RT for 1 h
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvents were removed in vacuo
  10. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient)

출처 및 근거

ORD 기록
ord-747f0697c3b5470eb5ef7c40241ce08a
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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