4-Chlorobenzoyl chloride → HCID 22475222, compound

HRID 2184121Notes

Reaction equation

[Cl-].[Cl-].[Cl-].[Al+3].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[F:15][C:16]1[CH:17]=[C:18]([O:22][CH3:23])[CH:19]=[CH:20][CH:21]=1>[N+](C1C=CC=CC=1)([O-])=O>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([C:21]2[CH:20]=[CH:19][C:18]([O:22][CH3:23])=[CH:17][C:16]=2[F:15])=[O:11])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Aluminium trichloride (144 g, 1.08 mol) was added to a cooled (0° C.) solution of nitrobenzene (450 mL). A solution of 4-chlorobenzoyl chloride (128.5 mL, 1 mol) in nitrobenzene (200 mL) was slowly added. 3-Fluoroanisole (108.5 mL, 0.95 mol) was slowly added. The reaction mixture was stirred overnight at 20° C., partitioned between ice water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic phase was washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The warm solution was poured onto cyclohexane. The solid was filtered, washed with cyclohexane and dried in vacuo, affording the title compound (104.5 g, 41%) as an off-white solid.

Workup

custompartitioned between ice water and ethyl acetate
extractionThe aqueous layer was extracted with ethyl acetate
washthe combined organic phase was washed with water
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
additionThe warm solution was poured onto cyclohexane
filtrationThe solid was filtered
washwashed with cyclohexane
customdried in vacuo

Sources & evidence

ORD record: ord-8416294b1e8b4e31ad98ef1a2a037792
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900227B2

Reaction notes

Loading…