Sodium Cyanide → 2-(3-Fluoro-2-hydroxyphenyl)acetonitrile

HRID 1176378ノート

反応式

HRID 1176378 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]O)[C:3]=1[OH:10].[C-:11]#[N:12].[Na+]>CN(C)C=O.O>[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH2:8][C:11]#[N:12])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 187554072-Fluoro-6-(hydroxymethyl)phenol

生成物 1

HCID 684994132-(3-Fluoro-2-hydroxyphenyl)acetonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4.89 g of 2-fluoro-6-hydroxymethylphenol and 2.08 g of sodium cyanide in 120 ml of N,N-dimethylformamide is stirred at 120° C. over 24 hours. The reaction mixture is cooled, diluted with water and concentrated by evaporation. The residue is diluted with water and neutralized with conc. acetic acid (caution! hydrocyanic acid). The mixture is extracted with dichloromethane (3×). The combined organic phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a violet solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.32 (1:2 EtOAc-heptane); Rt=3.12.

後処理

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated by evaporation
  3. additionThe residue is diluted with water and neutralized with conc. acetic acid (caution! hydrocyanic acid)
  4. extractionThe mixture is extracted with dichloromethane (3×)
  5. washThe combined organic phases are washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-1987e7beafb848b4a0afbc1d2dbac7db
出典データセット
uspto-grants-2010_11
特許番号
US07842688B2

反応ノート

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