Water → 5-fluoro-N-(3-fluorophenyl)-2-nitroaniline

HRID 2036580Notes

Reaction equation

HRID 2036580 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].F[C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18].CC(C)([O-])C.[K+].O>CN(C=O)C>[F:16][C:14]1[CH:13]=[CH:12][C:11]([N+:17]([O-:19])=[O:18])=[C:10]([CH:15]=1)[NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97423-FluoroanilineHCID 679672,4-DifluoronitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 584593185-fluoro-N-(3-fluorophenyl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-fluoroaniline (1.813 mL, 18.86 mmol) and 2,4-difluoro-1-nitrobenzene (1.723 mL, 15.71 mmol) in DMF (26.2 mL) was added potassium tert-butoxide (3.53 g, 31.4 mmol) under argon gas. The solution was stirred overnight at rt poured into water and extracted with DCM. The combined 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 an orange solid that was triturated in EtOAc:hexane (1:1) and filtered to give 5-fluoro-N-(3-fluorophenyl)-2-nitroaniline as an orange solid: LC-MS (ESI), m/z 251.1 [M+H]+.

Workup

  1. extractionextracted with DCM
  2. customThe combined organic extracts were purified by column chromatography on a silica gel column
  3. customto give an orange solid
  4. customthat was triturated in EtOAc:hexane (1:1)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-fbf3ed457f88416ca0677c401e9d9b0b
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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