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

HRID 1593616Notes

Reaction equation

HRID 1593616 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-e121c3f767dd490eb463a98701c63a91
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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