Hydrochloric Acid → 1-Chloro-2-nitro-4-[(trifluoromethyl)thio]benzene

HRID 2399732Notes

Reaction equation

HRID 2399732 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([S:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=1N)([O-:3])=[O:2].N(OC(C)(C)C)=O.O.[ClH:24]>C(#N)C.[Cu](Cl)Cl>[F:13][C:12]([F:15])([F:14])[S:11][C:9]1[CH:8]=[CH:7][C:5]([Cl:24])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10906Tert-Butyl nitriteHCID 23279174HCID 23279174, compound

Product 1

HCID 23391761-Chloro-2-nitro-4-[(trifluoromethyl)thio]benzene

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

2-Nitro-4-trifluoromethylthioaniline (0.5 g) in dry acetonitrile (3 cm3) was added over 0.5 hr. with stirring to copper (II) chloride (0.34 g) and tert-butyl nitrite (0.32 g) in dry acetonitrile (5 cm3) at 60° C. After 1 hr. the reaction was cooled to ambient temperature, poured into water, acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water (3×50 cm3) dried (magnesium sulphate) and evaporated under reduced pressure to give the required product as an oil; M+ =257; 1H NMR (CDCl3): δ7.65(d 1H); 7.80(dd 1H); 8.20(d 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water (3×50 cm3)
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fa880482393d4661b8c993281051cef7
Source dataset
uspto-grants-1995_09
Patent number
US05451594

Reaction notes

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