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

HRID 572583ノート

反応式

HRID 572583 の反応式
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]

参加物

4

反応物 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 2723810Sodium Formate

生成物 1

HCID 179928864-(2-Hydroxyacetyl)benzonitrile収率 50%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-514d75b9894e41878c9d71b65bb7679f
出典データセット
uspto-grants-2015_05
特許番号
US09029405B2

反応ノート

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