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

HRID 875335ノート

反応式

HRID 875335 の反応式
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

参加物

5

反応物 3

HCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate2 回HCID 86709824{4-[2-(4-Fluorophenyl)ethyl]phenyl}methanol

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e911f3f4d2824096948a971de7149160
出典データセット
uspto-grants-2015_03
特許番号
US08981104B2

反応ノート

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