Phenylacetyl chloride → HCID 11817819, compound

HRID 2298322Notes

Reaction equation

HRID 2298322 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9].[Cl-].[Al+3].[Cl-].[Cl-].[C:14]1([CH2:20][C:21](Cl)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([C:21](=[O:22])[CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[CH:4][C:3]=1[S:8][CH3:9]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 27747622-FluorothioanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11817819HCID 11817819, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.5 ml 2-fluorothioanisole in 50 ml dichloromethane, were added at 0° C. 1.2 g of aluminum chloride and 1 ml of phenylacetyl chloride. The reaction mixture was stirred for 12 hours at the room temperature. Then the reaction was quenched by adding appropriate amount of ice and aqueous HCl in one portion. The quenched mixture was extracted with dichloromethane (50 ml×3) and the organic layer was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, which was followed by removal of the magnesium sulfate by filtration. Then the filtrate was concentrated in vacuo and was purified by recrystallization from methanol to yield 1.8 g of 1-{3-fluoro-4-(methylthio)phenyl}-2-phenyl-ethan-1-one. mp: 71-72° C. NMR: δ2.50 (s, 3H), 4.22 (s, 2H), 7.20-7.33 (m, 6H), 7.64 (m, 1H), 7.77 (m, 1H). Step 2: Preparation of 2,2-dimethyl-5-{3-fluoro-4-(methylthio)phenyl}-4-phenyl-3(2H)-furanone

Workup

  1. customThen the reaction was quenched
  2. additionby adding appropriate amount of ice and aqueous HCl in one portion
  3. extractionThe quenched mixture was extracted with dichloromethane (50 ml×3)
  4. washthe organic layer was washed with brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate, which
  6. customwas followed by removal of the magnesium sulfate by filtration
  7. concentrationThen the filtrate was concentrated in vacuo
  8. customwas purified by recrystallization from methanol

Sources & evidence

ORD record
ord-28dee224b4f34188bd5b7764cf70db32
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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