Trifluoroacetic acid → 5-Chloro-alpha-(2-chlorophenyl)-2-(trifluoroacetylamino)benzyl alcohol

HRID 1793Notes

Reaction equation

HRID 1793 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].[F:18][C:19]([F:24])([F:23])[C:20](O)=[O:21].C(=O)([O-])O.[Na+]>ClCCl>[Cl:17][C:14]1[CH:15]=[CH:16][C:2]([NH:1][C:20](=[O:21])[C:19]([F:24])([F:23])[F:18])=[C:3]([CH:13]=1)[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 11437092(2-Amino-5-chlorophenyl)(2-chlorophenyl)methanol

Product 1

HCID 539916235-Chloro-alpha-(2-chlorophenyl)-2-(trifluoroacetylamino)benzyl alcoholYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.0 g of 2-amino-5-chloro-α-(2-chlorophenyl)benzyl alcohol in 12 ml of dichloromethane, a solution of 0.8 g of anhydrous trifluoroacetic acid in 2 ml of dichloromethane was added. After reaction, an aqueous solution of sodium hydrogen carbonate was added, and the organic layer was dried, after which the solvent was removed and the residue was recrystallized from hexane to yield 1.3 g of a crystal.

Workup

  1. customAfter reaction
  2. customthe organic layer was dried
  3. customafter which the solvent was removed
  4. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-39af1e12beb24e17a8267182051aa7af
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Reaction notes

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