Hydrochloric Acid → 2-(3-Fluorophenyl)-1-(4-(methylthio)phenyl)ethanone

HRID 2298314ノート

反応式

HRID 2298314 の反応式
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[F:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21](Cl)=[O:22])[CH:17]=[CH:18][CH:19]=1.Cl>ClCCl>[F:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([C:4]2[CH:5]=[CH:6][C:1]([S:7][CH3:8])=[CH:2][CH:3]=2)=[O:22])[CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7520ThioanisoleHCID 6451240Aluminum(III) ChlorideHCID 127516352-(3-Fluorophenyl)acetyl chloride

生成物 1

HCID 118178202-(3-Fluorophenyl)-1-(4-(methylthio)phenyl)ethanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 68 ml thioanisole in 600 ml dichloromethane at 0° C., were added slowly in a series aluminum chloride (77.3 g) and (3-fluorophenyl)acetyl chloride (100 g). The reaction mixture was stirred for an hour, after which 1 L of aqueous HCl was added slowly to the reaction mixture. The quenched mixture was stirred for another hour, which was followed by extraction with methylene chloride. The organic layer was washed with brine and then was dried over anhydrous magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resulting residue was purified by recrystallization from hexane/dichloromethane to yield 142.9 g of 2-(3-fluorophenyl)-1-{4-(methylthio)-phenyl}-ethanone. mp: 94.5-95.5° C. NMR: δ2.52 (s, 3H), 4.23 (s, 2H), 6.95-7.05 (m, 3H),7.25-7.30 (m, 3H), 7.92 (d, J=8.7 Hz, 2H).

後処理

  1. stirringThe quenched mixture was stirred for another hour
  2. extractionwhich was followed by extraction with methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by recrystallization from hexane/dichloromethane

出典と根拠

ORDレコード
ord-a96cfae41096487687b39e0cb4228108
出典データセット
uspto-grants-2002_12
特許番号
US06492416B1

反応ノート

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