Water → HCID 58459279, compound

HRID 2036583Notes

Reaction equation

HRID 2036583 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:17]=[C:18]([F:20])[CH:19]=1)[NH2:16].CC(C)([O-])C.[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[NH:16][C:15]1[CH:14]=[C:13]([F:12])[CH:19]=[C:18]([F:20])[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 965953,5-DifluoroanilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 58459279HCID 58459279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-2-fluoro-1-nitrobenzene (2.500 g, 14.24 mmol) and 3,5-difluoroaniline (2.206 g, 17.09 mmol) in DMF (22.61 mL) was added potassium tert-butoxide (3.20 g, 28.5 mmol) under argon and the solution was stirred at rt overnight. The solution was poured into water and extracted with DCM, and the organic extracts were purified by column chromatography on a silica gel column using 5 to 10% gradient of EtOAc in hexane as eluent to give 5-chloro-N-(3,5-difluorophenyl)-2-nitroaniline as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 6.98 (tt, J=9.34, 2.20 Hz, 1H) 7.02-7.11 (m, 3H) 7.35 (d, J=2.15 Hz, 1H) 8.14 (d, J=9.00 Hz, 1H) 9.40 (s, 1H).

Workup

  1. extractionextracted with DCM
  2. customthe organic extracts were purified by column chromatography on a silica gel column

Sources & evidence

ORD record
ord-5fe1f521615941d1b7f4f66cb56f6eba
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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