Trifluoroacetic acid → 4-(2-Hydroxyacetyl)benzonitrile

HRID 572575Notes

Reaction equation

HRID 572575 reaction equation
FC(F)(F)C(O)=[O:4].[C:8]([C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)(=[O:10])[CH3:9].FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O>C(#N)C.O>[OH:4][CH2:9][C:8]([C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 740444'-CyanoacetophenoneHCID 102317Bis(trifluoroacetoxy)iodobenzene

Product 1

HCID 179928864-(2-Hydroxyacetyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Trifluoroacetic acid (3.5 mL; 47.1 mmol) was added to a solution of 4-acetylbenzonitrile (3.40 g; 23.4 mmol) and [bis-(trifluoroacetoxy)iodo]benzene (20.1 g; 46.7 mmol) in acetonitrile/water (5:1; 300 mL). The reaction mixture was heated under reflux for 18 hours. The solvent was removed in vacuo and the residue partitioned between DCM and 10% aqueous potassium carbonate. The organic phase was poured through a hydrophobic frit and the solvent evaporated in vacuo. The residue was purified by flash chromatography eluting with iso-hexane/EtOAc (10:1 to 4:1) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.04 (d, J=8.4 Hz, 2H), 7.84 (d, J=8.4 Hz, 2H), 4.91 (d, J=2 Hz, 2H), 3.37 (t, J=2.0 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between DCM and 10% aqueous potassium carbonate
  5. additionThe organic phase was poured through a hydrophobic frit
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with iso-hexane/EtOAc (10:1 to 4:1)

Sources & evidence

ORD record
ord-c12f07bddc7f4d62b6e5768a393c6996
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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