Nitric Acid → HCID 17883229, compound

HRID 845526Notes

Reaction equation

HRID 845526 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH:11]([F:13])[F:12].[N+:15]([O-])([OH:17])=[O:16].C(=O)(O)[O-].[K+]>ClCCl>[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:15]([O-:17])=[O:16])=[CH:6][C:5]=1[O:10][CH:11]([F:13])[F:12]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516893Potassium BicarbonateHCID 27695681,2-bis(difluoromethoxy)benzene

Product 1

HCID 17883229HCID 17883229, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 15 g of 1,2-bis(difluoromethoxy)-benzene and 15 ml of 100% strength nitric acid in 150 ml of dichloromethane is stirred at room temperature for 7 hours. The mixture is neutralized with potassium bicarbonate solution and the organic layer is separated off and chromatographed on silica gel by means of cyclohexane/ethyl acetate (4:1). 1,2-Bis-(Difluoromethoxy)-4-nitro-benzene is obtained. This is hydrogenated and acetylated analogously to Example 21a to give N-[3,4-bis(difluoromethoxy)-phenyl]acetamide (m.p. 81°-83° C.). Analogously to Example 21, furthermore, N-[4,5-bis(difluoromethoxy)-2-nitrophenyl]acetamide (m.p. 65°-67° C.), N-[4,5-bis(difluoromethoxy)-2-nitro]aniline (m.p. 107°-109° C.), 4,5-bis(difluoromethoxy)-1,2-phenylenediamine dihydrochloride and the title compound of m.p. 285°-287° C. (decomposition; from isopropanol) are obtained.

Workup

  1. customthe organic layer is separated off
  2. customchromatographed on silica gel by means of cyclohexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-478d46b9c0304c9896aaeaeb1b279ce1
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Reaction notes

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