1,2-Dichloro-4-nitrobenzene → alpha-(2-Chloro-4-nitrophenyl)-4-fluoro-alpha-methylbenzeneacetonitrile
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[Cl:11].[OH-].[K+].[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=1>N1C=CC=CC=1>[Cl:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:21]([CH3:24])([C:18]1[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=1)[C:22]#[N:23]Participants
Conditions
- Temperature
- 5 °C
Procedure
To a stirred solution of 20 parts of 1,2-dichloro-4-nitrobenzene in 160 parts of pyridine was added a paste of 28 parts of solid potassium hydroxide and 40 parts of pyridine. After cooling to 5° C., there was added dropwise 15.6 parts of 4-fluoro-α-methylbenzeneacetonitrile. Upon completion, the whole was further stirred for 10 hours at -5° C. The cooling bath was removed and the reaction mixture was diluted with 80 parts of benzene. The whole was filtered and the filtrate was evaporated. The residue was poured into water and the product was extracted with methylbenzene. The latter was dried, filtered and evaporated. The solid residue was crystallized from a mixture of 1,1'-oxybisethane and benzene, yielding 15 parts of α-(2-chloro-4-nitrophenyl)-4-fluoro-α-methylbenzeneacetonitrile; mp. 133.1° C. (intermediate 2).
Workup
- customThe cooling bath was removed
- additionthe reaction mixture was diluted with 80 parts of benzene
- filtrationThe whole was filtered
- customthe filtrate was evaporated
- additionThe residue was poured into water
- extractionthe product was extracted with methylbenzene
- customThe latter was dried
- filtrationfiltered
- customevaporated
- customThe solid residue was crystallized from a mixture of 1,1'-oxybisethane and benzene
Sources & evidence
- ORD record
- ord-2e4fce10581a4fa7bb815b3ab7232393
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04778887
Reaction notes
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