Hydrochloric Acid → 3-(Chloromethyl)-5-fluorobenzo[b]-thiophene

HRID 1368896ノート

反応式

HRID 1368896 の反応式
C=O.[F:3][C:4]1[CH:12]=[CH:11][C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=1.[C:13]1(C)C=CC=CC=1.[ClH:20]>C(OCC)(=O)C.[Cl-].[Cl-].[Zn+2]>[Cl:20][CH2:13][C:10]1[C:6]2[CH:5]=[C:4]([F:3])[CH:12]=[CH:11][C:7]=2[S:8][CH:9]=1

参加物

7

反応物 4

HCID 313Hydrochloric Acid2 回HCID 712FormaldehydeHCID 1140TolueneHCID 118159505-Fluoro-1-benzothiophene

生成物 1

HCID 185181753-(Chloromethyl)-5-fluorobenzo[b]-thiophene収率 82.6%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-10 °C

実験手順

A mixture of formol (37%; 31 g) and ZnCl2 (10 g) in ethyl acetate (90 ml) and HCl (12 N; 190 ml) was stirred at −10° C. HCl (gas) was allowed to bubble through the mixture until saturation (at −10° C.). 5-Fluoro-benzo[b]thiophene (0.35 mol) was added dropwise at <0° C. The reaction mixture was stirred overnight at room temperature. Toluene (200 ml) was added and the mixture was stirred vigorously. The organic layer was separated, washed with an aqueous NaHCO3 solution and with water, dried, filtered and the solvent was evaporated. The residue was triturated under hexane, filtered off and dried, yielding 58 g (82.6%) of 3-(chloromethyl)-5-fluorobenzo[b]-thiophene (interm 11).

後処理

  1. customto bubble through the mixture until saturation (at −10° C.)
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. stirringthe mixture was stirred vigorously
  4. customThe organic layer was separated
  5. washwashed with an aqueous NaHCO3 solution and with water
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was triturated under hexane
  10. filtrationfiltered off
  11. customdried

出典と根拠

ORDレコード
ord-2e647644c8d84a169e1656e58c60d9bb
出典データセット
uspto-grants-2003_06
特許番号
US06576640B1

反応ノート

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