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

HRID 572583노트

반응식

HRID 572583 반응식
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]

참가 물질

4

반응물 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 2723810Sodium Formate

생성물 1

HCID 179928864-(2-Hydroxyacetyl)benzonitrile수율 50%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-514d75b9894e41878c9d71b65bb7679f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029405B2

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