Acetic Acid → 2-{4-[(2,4-Dichlorobenzyl)amino]phenyl}-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 2184089Notes

Reaction equation

HRID 2184089 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=1[CH:21]=O.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Cl:18][C:19]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=1[CH2:21][NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 134042,4-DichlorobenzaldehydeHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 5003444Sodium cyanoborohydride

Product 1

HCID 224756102-{4-[(2,4-Dichlorobenzyl)amino]phenyl}-1,1,1,3,3,3-hexafluoropropan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (Oakwoood, 1 g, 3.9 mmol) and 2,4-dichlorobenzaldehyde in methanol (21 mL) was stirred at ambient temperature. After 18 hours, glacial acetic acid (0.24 mL, 4.25 mmol) and sodium cyanoborohydride (388 mg, 4.25 mmol) were added. After stirring an additional 18 hours, the mixture was concentrated in vacuo and the residue dissolved in EtOAc. The organic layer was washed several times with brine, dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography (4:1 hexanes/EtOAc) afforded the title compound as a white waxy solid (1.6 g, 99%). MS (ES+) m/z 418 (M+), 420 (M+2).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe organic layer was washed several times with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-23e61819485b4ddb9281602ae4231e89
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

Loading…