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

HRID 1368896노트

반응식

HRID 1368896 반응식
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

참가 물질

7

반응물 4

HCID 313Hydrochloric Acid2회HCID 712FormaldehydeHCID 1140TolueneHCID 118159505-Fluoro-1-benzothiophene

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
-10 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2e647644c8d84a169e1656e58c60d9bb
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06576640B1

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