Acetyl chloride → 1-(3-Fluoro-4-methoxyphenyl)ethan-1-one
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 was added acetyl chloride (51.0 g, 0.65 mol) dropwise, maintaining the temperature between 5°-10° C. The mixture was allowed to stir for 10 minutes at 5° C. before the dropwise addition at 5°-10° C. of 2-fluoroanisole (63.06 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 methylene chloride (2×250 mL). The combined organic layers were washed with water (2×150 mL), dried over magnesium sulfate, and concentrated to 300 mL. Hexanes crystallized from the mixture: mp 92°-94° C.; 1H NMR (d6-DMSO) 7.8 (m, 2H), 7.3 (t, J=8.7Hz, 1H), 3.9 (s, 3H), 2.5 (s, 3H).
Workup
- customfitted with a mechanical stirrer
- temperaturecooled by means of an ice bath
- temperaturemaintaining the temperature between 5°-10° C
- customThe resultant layers were separated
- extractionthe aqueous layer was extracted with methylene chloride (2×250 mL)
- washThe combined organic layers were washed with water (2×150 mL)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated to 300 mL
- customHexanes crystallized from the mixture
Sources & evidence
- ORD record
- ord-fc2de7eae42f49f0a11bfcac06f22eb2
- Source dataset
- uspto-grants-2013_03
- Patent number
- USRE044048E1
Reaction notes
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