Nitric Acid → 106969-10-2

HRID 2309316Notes

Reaction equation

HRID 2309316 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[Cl:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[O:18][CH:19]([F:21])[F:20]>C(Cl)(Cl)Cl>[Cl:10][C:11]1[C:12]([O:18][CH:19]([F:20])[F:21])=[CH:13][C:14]([N+:1]([O-:4])=[O:2])=[C:15]([F:17])[CH:16]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 139610792-Chloro-1-(difluoromethoxy)-4-fluorobenzene

Product 1

HCID 13961080106969-10-2Yield 89.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To 21 g of conc. nitric acid was dropwise added 28 g of conc. sulfuric acid at 0° C., and the mixture was heated at 60° C. At intervals of 3 minutes, 10 g of 1-chloro-2-difluoromethoxy-5-fluorobenzene was added in 5 portions to the mixture, which was kept at 60° C. for half an hour. After cooling, the reaction mixture was poured on ice water and shaken with chloroform. The chloroform layer was washed with water, dried and concentrated. The residue was chromatographed on a column of silica gel, eluting with n-hexane-ethyl acetate (100:15 v/v). The eluate was concentrated to give 11 g of the titled compound XII-1.

Workup

  1. customat 0° C.
  2. waitwas kept at 60° C. for half an hour
  3. temperatureAfter cooling
  4. additionthe reaction mixture was poured on ice water
  5. washThe chloroform layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was chromatographed on a column of silica gel
  9. washeluting with n-hexane-ethyl acetate (100:15 v/v)
  10. concentrationThe eluate was concentrated

Sources & evidence

ORD record
ord-ab77e6f4ff46453aae01bba6b1af6565
Source dataset
uspto-grants-1987_09
Patent number
US04695312

Reaction notes

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