Hydrochloric Acid → 3,4-Difluoroaniline
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[CH:6][C:7]=1[F:8].Cl>CO.[Fe]>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[NH2:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
10 g of 3,4-difluoronitrobenzene was dissolved in 20 and 2 g of methanol and 10 g of concentrated hydrochloric acid and 2 g of iron powder were added thereto. The mixture was stirred at 60° C. for two hours, and then distilled to obtain 3,4-difluoroaniline. The reduction yield was 86%. To this product, 70 g of 36% hydrochloric acid was added to convert it into its salt. Under stirring, 18 g of a 25% NaNO2 aqueous solution was added at 0° C. to obtain a diazonium salt. The diazonium salt was dropwise added to a hydrochloric acid solution of cupric chloride heated to 120° C., for thermal decomposition. The diazotization yield was 84%. 3,4-Difluorochlorobenzene was obtained in an overall yield of 72%.
Workup
- additionwere added
- distillationdistilled
Sources & evidence
- ORD record
- ord-57f4299bf6914f95b4ae7e96640b0052
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05208394
Reaction notes
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