Cesium carbonate → 4-Bromo-5-(2,4-difluorophenoxy)-2-nitroaniline

HRID 629293Notes

Reaction equation

HRID 629293 reaction equation
[Br:1][C:2]1[C:8](F)=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[OH:27]>CS(C)=O.C(OCC)(=O)C.O>[Br:1][C:2]1[C:8]([O:27][C:21]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=2[F:19])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 219119284-Bromo-5-fluoro-2-nitroaniline

Product 1

HCID 1180936684-Bromo-5-(2,4-difluorophenoxy)-2-nitroanilineYield 95%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-bromo-5-fluoro-2-nitroaniline (1.08 g, 4.60 mmol) [Combi-Blocks, AN-1501] and cesium carbonate (1.80 g, 5.52 mmol) in dimethyl sulfoxide (5.0 mL) was treated with 2,4-difluorophenol (0.90 mL, 5.53 mmol) [Acros Organics, 24320] and stirred at 80° C. for 30 min. The reaction mixture was diluted with ethyl acetate and water. The organic layer was separated and washed with water and brine, dried with magnesium sulfate, filtered, and concentrated to give the desired product (1.50 g, 95%) as a yellow solid that was used without further purification. LCMS calculated for C12H8BrF2N2O3 (M+H)+: m/z=345.0, 347.0. found: 345.0, 346.9.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e183e705ee4741d183ce4c1769604b31
Source dataset
uspto-grants-2016_04
Patent number
US09315501B2

Reaction notes

Loading…