Acetyl chloride → 5-Acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene

HRID 1899075Notes

Reaction equation

HRID 1899075 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:23](Cl)(=[O:25])[CH3:24]>C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[C:23]([C:10]1[S:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 103368732-(4-Fluorophenyl)-3-(4-methylsulfonylphenyl)thiophene

Product 1

HCID 106431405-Acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent

Procedure

Titanium (IV) chloride (2.7 ml) was added dropwise to a stirred solution of 2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (5 g) and acetyl chloride (2.2 ml) in benzene (50 ml) at 5° to 10° C. The mixture was stirred at ambient temperature for 4 hours, poured into ice-water, and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium bicarbonate, dried and concentrated. The residue was recrystallized from a mixture of ethanol and ethyl acetate to give pale brown crystals of 5-acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (3.7 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium bicarbonate
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-58ff8d5d259143569ff59977789d45db
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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