Dichloromethane → HCID 19779402, compound

HRID 2082041Notes

Reaction equation

HRID 2082041 reaction equation
[Br:1]Br.[F:3][CH:4]([F:16])[O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1.O.O.O.C([O-])(=O)C.[Na+].ClCCl>C(Cl)(Cl)(Cl)Cl>[Br:1][C:11]1[C:9]([NH2:10])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=[C:6]([O:5][CH:4]([F:16])[F:3])[CH:12]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24408BromineHCID 159060344‐(Difluoromethoxy)‐2‐nitroanilineHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 19779402HCID 19779402, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Bromine (10 cm3) was added to a stirred suspension of 4-difluoromethoxy-2-nitroaniline (available as described for example in Example B5(b) of U.S. Pat. No. 4,686,230.) (26.6 g) and sodium acetate trihydrate (19.5 g) in carbon tetrachloride (250 mls). After stirring at ambient temperature for a period of 30 minutes, the reaction mixture was added to dichloromethane (350 mls) and washed with aqueous sodium metabisulphite solution, followed by aqueous sodium bicarbonate solution, and finally brine. The organic layer was the dried over anhydrous magnesium sulphate, and removal of the solvent by evaporation under reduced pressure, gave 6-bromo-4-difluoromethoxy-2-nitroaniline as an orange-brown solid. Melting Point: 60.5°-61.5° C. (cyclohexane).

Workup

  1. washwashed with aqueous sodium metabisulphite solution
  2. dry with materialdried over anhydrous magnesium sulphate, and removal of the solvent by evaporation under reduced pressure

Sources & evidence

ORD record
ord-243e550edfdc4b5c87966fe2a2b79bfb
Source dataset
uspto-grants-1993_02
Patent number
US05187176

Reaction notes

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