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

HRID 2084709Notes

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

Conditions

Temperature: 7.5 °C

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 200 mL. Hexanes were added and a white solid (77.2 g, 92%) was crystallized from the mixture: mp 92-94° C.; 1NMR (d6-DMSO) 7.8 (m, 2H), 7.3 (t, J=8.7 Hz, 1H), 3.9 (s, 3H), 2.5 (s, 3H).

Workup

customfitted with a mechanical stirrer
temperaturecooled by means of an ice bath
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 200 mL
additionHexanes were added
customa white solid (77.2 g, 92%) was crystallized from the mixture

Sources & evidence

ORD record: ord-7037148e274c4ecfadcbd137476732d8
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716991B1

Reaction notes

Loading…