Hydrochloric Acid → 3-Chloro-2,4-difluoroaniline

HRID 413044Notes

Reaction equation

HRID 413044 reaction equation
[Sn](Cl)Cl.[Cl:4][C:5]1[C:6]([F:15])=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][C:10]=1[F:11].Cl.[OH-].[Na+]>O.C(OCC)C>[Cl:4][C:5]1[C:6]([F:15])=[C:7]([CH:8]=[CH:9][C:10]=1[F:11])[NH2:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 2230803-Chloro-2,4-difluoronitrobenzene

Product 1

HCID 2230893-Chloro-2,4-difluoroanilineYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

135 g of tin(II) chloride (dihydrate) was added in small fractions to a stirred suspension of 23 g of 3-chloro-2,4-difluoronitrobenzene in 110 cm3 of a 37% aqueous hydrochloric acid solution and 25 cm'of diethyl ether. After the addition, the mixture was heated for 30 minutes at a temperature in the region of 40° C. After cooling the reaction mass, the mixture was poured over 300 cm3 of water supplemented with 150 g of ice. The mixture was made highly alkaline by addition of caustic soda, and then extracted twice with 250 cm3 of chloroform. The extracts were combined, dried over magnesium sulphate, and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 17.4 g of 3-chloro-2,4-difluoroaniline was obtained in the form of a beige solid, which melted at 58° C.

Workup

  1. additionAfter the addition
  2. temperatureAfter cooling the reaction mass
  3. extractionextracted twice with 250 cm3 of chloroform
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-c5e95ce26978405ab110f04fa674c236
Source dataset
uspto-grants-2003_05
Patent number
US06566362B2

Reaction notes

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