Hydrochloric Acid → (4-Fluoro-3-nitrophenyl)(phenyl)methanone
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16].Cl>C1C=CC=CC=1>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([C:6]2[CH:14]=[CH:13][CH:9]=[CH:8][CH:7]=2)=[O:11])=[CH:8][C:7]=1[N+:15]([O-:17])=[O:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a stirred mixture of 496 parts of aluminum chloride in 900 parts of benzene was added dropwise a solution of 256 parts of 4-fluoro-3-nitrobenzoyl chloride in 225 parts of benzene at ±10° C. Upon complete addition, stirring was continued first for 1.5 hours in an ice bath and then for 8 hours at room temperature. The mixture was heated to 60° C., cooled again and poured into crushed ice and 180 parts of concentrated hydrochloric acid. The separated organic layer was dried, filtered and concentrated. The concentrate was dissolved in 2100 parts of 2,2'-oxybispropane, the solution was treated with diatomaceous earth and activated charcoal. After filtration, the filtrate was concentrated. The crystallized product was filtered off and dried, yielding 223 parts (73%) of (4-fluoro-3-nitrophenyl) phenylmethanone; mp. 59° C. (int. 62).
Workup
- additionUpon complete addition
- waitfor 8 hours at room temperature
- temperaturecooled again
- additionpoured
- customThe separated organic layer was dried
- filtrationfiltered
- concentrationconcentrated
- dissolutionThe concentrate was dissolved in 2100 parts of 2,2'-oxybispropane
- additionthe solution was treated with diatomaceous earth and activated charcoal
- filtrationAfter filtration
- concentrationthe filtrate was concentrated
- filtrationThe crystallized product was filtered off
- customdried
Sources & evidence
- ORD record
- ord-b1552b184b294fe79f9da68c43c542c5
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04943574
Reaction notes
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