Sodium Cyanide → 6-Fluoropyridine-2-carbonitrile

HRID 911314ノート

反応式

HRID 911314 の反応式
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[C-:9]#[N:10].[Na+]>CS(C)=O.CCOC(C)=O>[C:9]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1)#[N:10]

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 739342,6-Difluoropyridine

生成物 1

HCID 142963696-Fluoropyridine-2-carbonitrile収率 22.3%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

Dissolve 2,6-difluoropyridine (12 g, 104.2 mmol) in anhydrous DMSO (5 mL). Add a solution of sodium cyanide (1.3 g, 26.53 mmol) in DMSO (60 mL) over 12 h using a syringe pump. Heat the mixture to 100° C. overnight. Cool to ambient temperature, dilute with EtOAc (500 mL), and wash with brine. Dry the organic phase over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 4:1) to give the desired intermediate as a solid (723 mg, 22%). GC-MS m/z: 122 (M+).

後処理

  1. temperatureCool to ambient temperature
  2. washwash with brine
  3. dry with materialDry the organic phase over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 4:1)

出典と根拠

ORDレコード
ord-30c0b381036a416698de588058f2eb44
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

反応ノート

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