HCID 21392401, compound → HCID 53889307, compound

HRID 461764Notes

Reaction equation

HRID 461764 reaction equation
[F:1][C:2]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])(Cl)[C:3]([F:6])(Cl)[Cl:4]>[Zn].C(O)C>[Cl:4][C:3]([F:6])=[C:2]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])[F:1]

Participants

4

Reactant 1

HCID 21392401HCID 21392401, compound

Product 1

HCID 53889307HCID 53889307, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

74 G. of zinc dust is added to a vigorously stirred solution of 40 g. of 3-(1,2-difluoro-1,2,2-trichloroethyl)-aniline in 450 ml. of ethanol and heated at reflux for 2 hours. It is filtered hot, the solid residue washed with hot ethanol and the combined ethanol solution cooled to room temperature. About 1000 ml. of chloroform is added and the organic layer is washed with aqueous NaHCO3 solution and with water, dried over Na2SO4 and concentrated in vacuo to 23.9 g. of oily 3-(2-chloro-1,2-difluorovinyl)aniline. This gives a single peak with a retention time of 1.8 minutes at 200° C. on a gas liquid chromatography column packed with 5% SE30, and the correct values for C,H,N,Cl and F by combustion analysis.

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationIt is filtered hot
  3. washthe solid residue washed with hot ethanol
  4. additionof chloroform is added
  5. washthe organic layer is washed with aqueous NaHCO3 solution and with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo to 23.9 g
  8. customThis gives a single peak with a retention time of 1.8 minutes at 200° C. on a gas liquid chromatography column

Sources & evidence

ORD record
ord-b062fa6b7b804f548586e168392e927b
Source dataset
uspto-grants-1977_12
Patent number
US04064239

Reaction notes

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