Hydrochloric Acid → 2-(3-Fluorophenyl)-1-(4-(methylthio)phenyl)ethanone

HRID 2298314Notes

Reaction equation

HRID 2298314 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[F:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21](Cl)=[O:22])[CH:17]=[CH:18][CH:19]=1.Cl>ClCCl>[F:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([C:4]2[CH:5]=[CH:6][C:1]([S:7][CH3:8])=[CH:2][CH:3]=2)=[O:22])[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7520ThioanisoleHCID 6451240Aluminum(III) ChlorideHCID 127516352-(3-Fluorophenyl)acetyl chloride

Product 1

HCID 118178202-(3-Fluorophenyl)-1-(4-(methylthio)phenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 68 ml thioanisole in 600 ml dichloromethane at 0° C., were added slowly in a series aluminum chloride (77.3 g) and (3-fluorophenyl)acetyl chloride (100 g). The reaction mixture was stirred for an hour, after which 1 L of aqueous HCl was added slowly to the reaction mixture. The quenched mixture was stirred for another hour, which was followed by extraction with methylene chloride. The organic layer was washed with brine and then was dried over anhydrous magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resulting residue was purified by recrystallization from hexane/dichloromethane to yield 142.9 g of 2-(3-fluorophenyl)-1-{4-(methylthio)-phenyl}-ethanone. mp: 94.5-95.5° C. NMR: δ2.52 (s, 3H), 4.23 (s, 2H), 6.95-7.05 (m, 3H),7.25-7.30 (m, 3H), 7.92 (d, J=8.7 Hz, 2H).

Workup

  1. stirringThe quenched mixture was stirred for another hour
  2. extractionwhich was followed by extraction with methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by recrystallization from hexane/dichloromethane

Sources & evidence

ORD record
ord-a96cfae41096487687b39e0cb4228108
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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