Methanol → 4-Bromo-5-fluoro-2-nitroaniline

HRID 1429206Notes

Reaction equation

HRID 1429206 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9]C(=O)C(F)(F)F)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.CO.C([O-])([O-])=O.[K+].[K+]>O>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH2:9])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 59821153HCID 59821153, compound

Product 1

HCID 219119284-Bromo-5-fluoro-2-nitroanilineYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To N-(4-bromo-5-fluoro-2-nitrophenyl)-2,2,2-trifluoroacetamide (3.5 g, 10.5 mmol) was added CH3OH (30 mL) followed by 1.0 M K2CO3 (10.5 mL, 10.5 mmol), and the solution was stirred for 30 minutes (Charifson, P. S.; et al. J. Med. Chem. 2008, 51, 5243-5263). The solution was diluted with H2O and stirred for 1 hour. The resulting orange solid was collected by filtration and dried in a vacuum oven to give the title compound (2.1,g, 8.8 mmol, 84%).

Workup

  1. stirringstirred for 1 hour
  2. filtrationThe resulting orange solid was collected by filtration
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d693d5f4422b433a909bd61b2fec232f
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

Loading…