Hydrochloric Acid → Ethyl 8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylate

HRID 1593616노트

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HRID 1593616 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][C:10]2=O)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClC(Cl)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[S:8][C:9]3[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][C:10]=3[C:4]=2[CH:3]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 69232235Ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylate

생성물 1

HCID 69235740Ethyl 8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylate수율 78.1%

시약·촉매·용매 2

HCID 962Water용매HCID 63651,1-Dichloroethane용매

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온도
80 °C

실험 절차

To a room temperature solution of ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylate (3.4 g, 11.5 mmol) in dichloroethane (100 mL) was added AlCl3 (3.7 g, 27.6 mmol). The mixture was heated to 80° C. for 1 hour. After cooling to room temperature, the reaction was diluted with water and acidified with 1 N HCl. The aqueous mixture was extracted with EtOAc. The organic layer was washed with water then brine, then was dried over MgSO4 and concentrated to an oil. Purification by chromatography on silica gel afforded 2.5 g (77%) of the title compound as semi-solid: MS (+) 278 (M)+.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous mixture was extracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialbrine, then was dried over MgSO4
  5. concentrationconcentrated to an oil
  6. customPurification by chromatography on silica gel

출처 및 근거

ORD 기록
ord-e121c3f767dd490eb463a98701c63a91
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297704B2

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