Acetyl chloride → 1-(3-Fluoro-4-methoxyphenyl)ethan-1-one
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 7.5 °C
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
- customThe resultant layers were separated
- extractionthe aqueous layer was extracted with dichloromethane (2×250 mL)
- washThe combined organic layers were washed with water (2×150 mL)
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo to a volume of 300 mL
- additionHexanes were added
- customa white solid formed which
- customwas isolated by filtration and air
- customdried
- customThis material was recrystallized from a mixture of dichloromethane and hexanes
Sources & evidence
- ORD record
- ord-f49f817a1e6f4015a77be128c4f7b86c
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05990148
Reaction notes
Loading…