Nitromethane → 4-Chloro-2-fluoroaniline

HRID 648287Notes

Reaction equation

HRID 648287 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1C(O)=O.[OH-].[Na+].C[N+:15]([O-])=O>>[F:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[NH2:15]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 991524-Chloro-2-fluorobenzoic acid

Product 1

HCID 938984-Chloro-2-fluoroaniline

Procedure

A mixture of 2-fluoro-4-chlorobenzoic acid (6.05 g), polyphosphoric acid (62.51 g) and CH3NO2 (5.1 g) is heated at 130°. After about 2.5 hr, the reaction mixture is poured onto ice and made basic by addition of dilute sodium hydroxide. The reaction is then worked up by extracting with ether. The combined ether extracts are washed with water and brine, dried over sodium sulfate, filtered and evaporated to yield 2-fluoro-4-chloroaniline.

Workup

  1. temperatureis heated at 130°
  2. additionthe reaction mixture is poured onto ice
  3. extractionby extracting with ether
  4. washThe combined ether extracts are washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8e1d85b9e0da4595ab70c78a85cdf0db
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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