Methyl 3-fluoro-4-nitrobenzoate → Methyl 3-[[3-chloro-4-(trifluoromethoxy)phenyl]amino]-4-nitrobenzoate

HRID 452668Notes

Reaction equation

HRID 452668 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[O:23][C:24]([F:27])([F:26])[F:25])[NH2:19]>CS(C)=O.C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6])[CH:20]=[CH:21][C:22]=1[O:23][C:24]([F:26])([F:27])[F:25]

Participants

5

Reactant 2

HCID 592761Methyl 3-fluoro-4-nitrobenzoateHCID 27738433-Chloro-4-(trifluoromethoxy)aniline

Product 1

HCID 68662839Methyl 3-[[3-chloro-4-(trifluoromethoxy)phenyl]amino]-4-nitrobenzoateYield 38%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-fluoro-4-nitrobenzoate (1.99 g, 10 mmol) and 3-chloro-4-(trifluoromethoxy)aniline (4.23 g, 20 mmol) in dimethylsulfoxide (10 mL) was stirred at 160° C. for 2 days. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) and recrystallized from hexane/ethyl acetate to give the title compound (1.47 g, yield 38%) as orange crystals.

Workup

  1. temperatureAfter cooling
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)
  6. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-e627c0574fc34a9d829d9a8702b2a97b
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

Loading…