Thionyl Chloride → 1-(Chloromethyl)-4-[2-(4-fluorophenyl)ethyl]benzene

HRID 875335노트

반응식

HRID 875335 반응식
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:3][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][C:9]2[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=2)=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate2회HCID 86709824{4-[2-(4-Fluorophenyl)ethyl]phenyl}methanol

생성물 1

HCID 220150131-(Chloromethyl)-4-[2-(4-fluorophenyl)ethyl]benzene

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

At 0° C., 14.96 ml of thionyl chloride in 100 ml of dichloromethane were slowly added dropwise to a solution of 31.5 g (136.7 mmol) of {4-[2-(4-fluorophenyl)ethyl]phenyl}methanol in 400 ml of dichloromethane. After the addition had ended, the reaction mixture was warmed to room temperature and stirred at this temperature for another 2 hours. The reaction mixture was then once more cooled to 0° C., and 200 ml of saturated aqueous sodium bicarbonate solution were added slowly and carefully, with vigorous stirring. Subsequently, small portions of solid sodium bicarbonate were added to the solution until the pH had been adjusted to 6. The phases were then separated, and the organic phase was dried over magnesium sulphate, filtered and concentrated to dryness. This gave 28.5 g (114.5 mmol, 84% of theory) of the title compound.

후처리

  1. additionAfter the addition
  2. temperatureThe reaction mixture was then once more cooled to 0° C.
  3. customThe phases were then separated
  4. dry with materialthe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-e911f3f4d2824096948a971de7149160
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981104B2

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