Water → HCID 2759000, compound

HRID 2378065Notes

Reaction equation

HRID 2378065 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13].[C:14]1([CH2:20][C:21](Cl)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>ClCCl>[F:5][C:6]1[CH:11]=[C:10]([C:21](=[O:22])[CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:7]=1[O:12][CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 675762-FluoroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2759000HCID 2759000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a stirring suspension consisting of aluminum trichloride (15.9 g) in dichloromethane (200 mL) cooled to an internal temperature of −10° C. under a nitrogen atmosphere is added 2-fluoroanisole (10 g) over one minute. Phenylacetyl chloride (11.6 mL) is subsequently added to the mixture at a rate that maintained the internal temperature below 0° C. The reaction mixture is allowed to warm to room temperature overnight. Water (100 mL) is cautiously added to the stirring mixture. The layers are subsequently separated and the dichloromethane layer is concentrated under reduced pressure. The concentrate is dissolved in ethyl acetate and washed with water, 1 M sodium hydroxide, water, and brine. The organic layer is dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford the synthetic intermediate 1-(3-fluoro-4-methoxy-phenyl)-2-phenyl-ethanone (14.1 g.)

Workup

  1. temperaturethat maintained the internal temperature below 0° C
  2. temperatureto warm to room temperature overnight
  3. customThe layers are subsequently separated
  4. concentrationthe dichloromethane layer is concentrated under reduced pressure
  5. dissolutionThe concentrate is dissolved in ethyl acetate
  6. washwashed with water, 1 M sodium hydroxide, water, and brine
  7. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57517fa356304786a0cffb9bf89ead20
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

Loading…