4-Chlorobenzoyl chloride → HCID 22475222, compound
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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-7e5354e72943453f923d4d27aecc0973
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576088B2
Reaction notes
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