Trifluoroacetic acid → 3,4-Dichloro-α-(trifluoromethyl)benzenemethanamine

HRID 2279481Notes

Reaction equation

HRID 2279481 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:14]CC2C=CC(OC)=C(OC)C=2)[C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH2:14])[C:10]([F:11])([F:12])[F:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86705490HCID 86705490, compound

Product 1

HCID 433445253,4-Dichloro-α-(trifluoromethyl)benzenemethanamineYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 146 (4.11 g, 10.43 mmol) in DCM (50 mL) was added TFA (2.410 ml, 31.28 mmol) and reaction was stirred for 18 hr at RT. The reaction mixture was concentrated and dissolved in DCM. A solution of HCl (20 mL, 2M Et2O) was added and the solvent was decanted from the solids. The solids were dissolved in 15% MeOH/DCM and saturated NaHCO3 was added. The organic layer was separated and concentrated. The residue was triturated with EtOAc and allowed to stand. The resulting solids were filtered to afford 1.904 g (74.8%) of 1-(3,4-dichlorophenyl)-2,2,2-trifluoroethanamine (148).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in DCM
  3. additionA solution of HCl (20 mL, 2M Et2O) was added
  4. customthe solvent was decanted from the solids
  5. dissolutionThe solids were dissolved in 15% MeOH/DCM
  6. additionsaturated NaHCO3 was added
  7. customThe organic layer was separated
  8. concentrationconcentrated
  9. customThe residue was triturated with EtOAc
  10. filtrationThe resulting solids were filtered

Sources & evidence

ORD record
ord-7baad39520124a119f7651288fc7fbe0
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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