Hydrogen Bromide → HCID 67169821, compound

HRID 1918358Notes

Reaction equation

HRID 1918358 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]2[CH2:14][C:13]([F:16])([F:15])[CH2:12]2)=[C:6](N)[CH:5]=1.N([O-])=O.[Na+].[BrH:23]>O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]2[CH2:14][C:13]([F:16])([F:15])[CH2:12]2)=[C:6]([Br:23])[CH:5]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 23668193Sodium NitriteHCID 67170012HCID 67170012, compound

Product 1

HCID 67169821HCID 67169821, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g of 3-Amino-4-(3,3-difluoro-cyclobutoxy)-benzoic acid methyl ester was dissolved in 100 ml of half-concentrated aqueous HBr-solution. Then, a solution of 295 mg NaNO2 in 5 ml of water was added dropwise at 0° C. Stirring was continued at 0° C. for 15 minutes. Then, a solution of 558 mg CuBr in 10 ml of half-concentrated aqueous HBr-solution was added dropwise and the reaction mixture was stirred for 2 h at room temperature. Then, the reaction mixture was extracted three times using 100 ml of EA each. The organic layer was then washed three times using 100 ml of a saturated aqueous NaHCO3-solution, dried using MgSO4 and volatiles were evaporated to yield 150 mg of the title compound that was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred for 2 h at room temperature
  2. extractionThen, the reaction mixture was extracted three times
  3. washThe organic layer was then washed three times
  4. customdried
  5. customwere evaporated

Sources & evidence

ORD record
ord-84fde5943ed644ce996f99f28eb942e4
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

Loading…