Sodium Cyanide → 6-Fluoropyridine-2-carbonitrile

HRID 2099511ノート

反応式

HRID 2099511 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>[F:8][C:4]1[N:3]=[C:2]([C:9]#[N:10])[CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 739342,6-Difluoropyridine

生成物 1

HCID 142963696-Fluoropyridine-2-carbonitrile

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

2,6 Difluoropyridine (12 g, 100 mmol) was dissolved in DMSO (3 mL) and sodium cyanide (1.3 g, 26 mmol) in DMSO (100 mL) was added dropwise via syringe pump over 16 h. The reaction was then heated at 100° C. for 16 h. The crude mixture was then diluted with EtOAc (500 mL) and washed with a mixture of brine (200 mL) and H2O (500 mL). The organic phase was dried (MgSO4), filtered, and concentrated in vacito. The residue was chromatographed on silica gel eluting with hexanes:EtOAc (4:1) to afford 6-fluoropyridine-2-carbonitrile. MS (ESI) 122.0 (M++H).

後処理

  1. washwashed with a mixture of brine (200 mL) and H2O (500 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacito
  5. customThe residue was chromatographed on silica gel eluting with hexanes:EtOAc (4:1)

出典と根拠

ORDレコード
ord-516d0035fee54c79901f11e149fc01d7
出典データセット
uspto-grants-2009_08
特許番号
US07569592B2

反応ノート

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