1,1-Dichloroethane → 4-Amino-3,5-dichlorobenzotrifluoride
Reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:13]C1C=CC(C(F)(F)F)=CC=1N.ClC(Cl)C.S(Cl)(Cl)(=O)=O.[OH-].[Na+]>O.CN1C(=O)CCC1>[Cl:1][C:2]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=[C:5]([Cl:13])[C:3]=1[NH2:4]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 55 °C
Procedure
A mixture (740 g) containing 2-chloro-4-trifluoromethyaniline, 2-chloro-5-trifluoromethylaniline and NMP (0.686 m/m) was charged with 400 ml dichloroethane in to the reactor. It was then heated to 55° C. and reacted with 430 g of sulfuryl chloride at 55-60° C. over a period of 4 hrs & further maintained at 65-70° C. for 2 hrs. The reaction mixture was worked up by adding water & treating with 5N NaOH, the organic layer was fractionated under reduced pressure to get 504.9 g of distilled 2,6-dichloro-4-trifluoromethylaniline. The yield of 2,6-dichloro-4-trifluoromethyl aniline was 93.5% on 2-chloro-4-trifluoromethylaniline.
Workup
- temperaturefurther maintained at 65-70° C. for 2 hrs
Sources & evidence
- ORD record
- ord-b25f4cf52a8c4f52bf04d00d502fa0a0
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507693B2
Reaction notes
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