Hydrochloric Acid → 3-(1,1-Difluoroethyl)aniline

HRID 2200192Notes

Reaction equation

HRID 2200192 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)OC2C=CC=CC=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])F.Cl.[OH-].[Na+].[CH2:25](O)C>[Fe]>[F:21][C:18]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:2]=1)[NH2:8])([F:20])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 13412531HCID 13412531, compound

Product 1

HCID 234450923-(1,1-Difluoroethyl)aniline

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Dissolve the nitro compound obtained in Step 1 (870 mg, 4.8 mmol) in ethanol (10 mL), add iron powder (1.3 g, 23.3 mmol), concentrated aqueous HCl (37%, 2.7 mL), stir the reaction at room temperature for 2 hrs. After the reaction, carefully neutralize the mixture with NaOH solution. Filter off the solid, pour the filtrate to ice water (50 mL), extract with EtOAc (15 mL×3), combine the organic layers, wash with brine (100 mL) and dry over anhydrous Na2SO4. Concentrate under reduced pressure to get the crude product (760 mg) which is used without further purification.

Workup

  1. customthe reaction at room temperature for 2 hrs
  2. customAfter the reaction
  3. filtrationFilter off the solid
  4. additionpour the filtrate to ice water (50 mL)
  5. extractionextract with EtOAc (15 mL×3)
  6. washwash with brine (100 mL)
  7. dry with materialdry over anhydrous Na2SO4
  8. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-69648884d92b42efab6f2e9652217f5f
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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