Phenylacetyl chloride → HCID 2759000, compound

HRID 1781438Notes

Reaction equation

HRID 1781438 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[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>C(Cl)(Cl)Cl>[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

5

Reactant 3

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

Product 1

HCID 2759000HCID 2759000, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 500 mL, 3-neck round-bottom flask, equipped with a pressure equalizing dropping funnel, thermometer, gas inlet tube and provisions for magnetic stirring, a suspension of aluminum chloride (9.4 g, 70.5 mmol) in a solution of 2-fluoroanisole (6.6 mL, 58.8 mmol) and anhydrous chloroform (200 mL) was cooled to 0° C. under a blanket of dry nitrogen. A solution of phenylacetyl chloride (8.6 mL, 64.7 mmol) in anhydrous chloroform (50 mL) was added to the vigorously stirred suspension over 20 minutes keeping the reaction temperature <5° C. The yellowish solution was stirred at 0° C. for 1 hour, then poured into ice (200 mL) and stirred without temperature control for 16 hours. The layers were separated, and the aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic solution was dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The resulting solid was recrystallized from boiling hexane to yield, upon filtration and drying, 12.9 g (90%) of 1-(3-fluoro-4 methoxyphenyl)-2-phenyl-ethan-1-one as white crystals: 1H NMR (CDCl3 /300 MHz) δ 7.82-7.72 (m, 2H), 7.35-7.24 (m, 5H), 6.98 (dd, J=8.46, 8.26 Hz, 1H), 4.22 (s, 2H), 3.94 (s, 3H). 19F NMR (CDCl3 /282.2 MHz) -134,875 (m).

Workup

  1. customIn a 500 mL, 3-neck round-bottom flask, equipped with a pressure
  2. customthe reaction temperature <5° C
  3. stirringstirred without temperature control for 16 hours
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with dichloromethane (2×100 mL)
  6. dry with materialThe combined organic solution was dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe resulting solid was recrystallized
  10. customto yield, upon filtration
  11. customdrying

Sources & evidence

ORD record
ord-a65d0fc87e374b819e92f28178044fe3
Source dataset
uspto-grants-1997_05
Patent number
US05633272

Reaction notes

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