4-(Bromoacetyl)benzonitrile → 4-(2-Hydroxyacetyl)benzonitrile

HRID 572583Notes

Reaction equation

HRID 572583 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1)=[O:4].C([O-])=[O:14].[Na+]>CO>[OH:14][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 2723810Sodium Formate

Product 1

HCID 179928864-(2-Hydroxyacetyl)benzonitrileYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-Bromo-1-(4-cyanophenyl)ethanone (15 g, 0.067 mol) in methanol (200 ml) was added sodium formate (13.6 g, 0.201 mol) at RT. The reaction mixture was refluxed for 15 h and filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved with ethyl acetate, washed with water and brine solution, dried over Na2SO4 and evaporated. The crude material was purified by column chromatography using petroleum ether and ethyl acetate (60:40) as an eluent to afford (5.4 g, 50%) of title compound as an off white solid. 1H NMR: (DMSO-d6, 400 MHz) δ 8.06-8.04 (dd, J=1.9, 6.7 Hz, 2H), 8.00-7.98 (dd, J=1.9, 6.7 Hz, 2H), 5.27-5.24 (t, J=5.9 Hz, 1H), 4.82-4.80 (d, J=5.9 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved with ethyl acetate
  5. washwashed with water and brine solution
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-514d75b9894e41878c9d71b65bb7679f
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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