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

HRID 1292300Notes

Reaction equation

HRID 1292300 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[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:5](=[O:7])[CH3:6])[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

Aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL) were placed in a 2 L three-necked round bottom flask fitted with a mechanical stirrer and cooled by means of an ice bath. To the stirred solution acetyl chloride (51.0 g, 0.65 mol) was added dropwise, maintaining the temperature between 5°-10° C. The mixture was stirred for 10 minutes at 5° C. before the dropwise addition at 5°-10° C. 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.; 1H NMR (DMSO-d6) 7.8 (m, 2H), 7.3 (t, 1H), 3.9 (s, 3H), 2.5 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-fa2d23817dbe4bce95d6a5f6044cb7b2
Source dataset
uspto-grants-1998_05
Patent number
US05756529

Reaction notes

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