Sodium Hydroxide → 4-Chloro-2-fluoroaniline

HRID 249429Notes

Reaction equation

HRID 249429 reaction equation
CC([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[F:12])=O.[OH-].[Na+]>C(O)C.O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([NH2:4])=[C:6]([F:12])[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 8531744'-Chloro-2'-fluoroacetanilide

Product 1

HCID 938984-Chloro-2-fluoroanilineYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 155 g (0.83 mole) of 4-chloro-2-fluoroacetanilide in 400 ml of ethanol was added dropwise a solution of 72.0 g (1.8 moles) of sodium hydroxide in 100 ml of water. Upon completion of addition the reaction mixture was heated under reflux for three hours. The reaction mixture was cooled to ambient temperature and extracted with diethyl ether. The combined extracts were concentrated under reduced pressure to a residual oil. The oil was distilled under reduced pressure to yield 81.0 g of 4-chloro-2-fluoroaniline; b.p. 83-85/12 mm. The reaction was repeated several times.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for three hours
  4. extractionextracted with diethyl ether
  5. concentrationThe combined extracts were concentrated under reduced pressure to a residual oil
  6. distillationThe oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-1e28b85af5b24c4396e3c7cd54d13326
Source dataset
uspto-grants-1993_05
Patent number
US05214154

Reaction notes

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