Acetyl chloride → 1-(3-Fluoro-4-methoxyphenyl)ethan-1-one

HRID 1940602Notes

Reaction equation

HRID 1940602 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17]>C(Cl)(Cl)Cl>[F:9][C:10]1[CH:15]=[C:14]([C:1](=[O:3])[CH3:2])[CH:13]=[CH:12][C:11]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 675762-FluoroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 968281-(3-Fluoro-4-methoxyphenyl)ethan-1-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acetyl chloride (51.0 g, 0.65 mol) was added dropwise to a stirred solution of aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL), maintaining the temperature between 5°-10° C. The mixture was stirred for 10 minutes at 5° C. before the dropwise addition of 2-fluoroanisole (62.6 g, 0.5 mol). The mixture was stirred at 0°-10° C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2×250 mL). The combined organic layers were washed with water (2×150 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 mL. Hexanes were added and a white solid formed which was isolated by filtration and air dried. This material was recrystallized from a mixture of dichloromethane and hexanes to afford (77.2 g, 92%) of material suitable for use in the next step: mp 92°-94° C.

Workup

  1. temperaturemaintaining the temperature between 5°-10° C
  2. customThe resultant layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (2×250 mL)
  4. washThe combined organic layers were washed with water (2×150 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a volume of 300 mL
  8. additionHexanes were added
  9. customa white solid formed which
  10. customwas isolated by filtration and air
  11. customdried
  12. customThis material was recrystallized from a mixture of dichloromethane and hexanes

Sources & evidence

ORD record
ord-b28e22d7f0ed4931acb7d9c457f7b87e
Source dataset
uspto-grants-1997_12
Patent number
US05700816

Reaction notes

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