Chloroacetonitrile → 2-(5-Bromo-2-chloropyridin-3-yloxy)acetonitrile

HRID 2077590ノート

反応式

HRID 2077590 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5]([Cl:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:17][C:18]#[N:19]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:17][C:18]#[N:19])[C:5]([Cl:8])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 7856ChloroacetonitrileHCID 10796Cesium carbonateHCID 167481065-Bromo-2-chloropyridin-3-ol

生成物 1

HCID 866279992-(5-Bromo-2-chloropyridin-3-yloxy)acetonitrile収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A dry 10 mL, one neck round bottom flask was charged with 5-bromo-2-chloropyridin-3-ol (0.0518 g, 0.249 mmol), cesium carbonate (0.0972 g, 0.298 mmol), a stirbar and 2 mL dry DMF. The stirring slurry was treated with 2-chloroacetonitrile (0.0709 ml, 1.12 mmol) and fitted with an inert atmosphere inlet. The reaction was heated to 80° C. using an oil bath for 3 h, and cooled. The slurry was filtered through a 0.22 μm PTFE filter, and concentrated in vacuo. The residue was purified in one injection using a YMC pack diol-120-NP column (PN DN12S05-2520 wt, 250×20 mm, spherical particle, 5 μm particle size, 120 Å pore size, flow=20 mL/min: A=hexanes; B=THF; 15% B isocratic). A fraction that eluted from 10.0 to 11.8 minutes was isolated. The solvent was removed in vacuo to afford 2-(5-bromo-2-chloropyridin-3-yloxy)acetonitrile (0.0375 g, 61.0% yield). 1H NMR (300 MHz, chloroform-d) δ ppm 4.88 (s, 2H) 7.52 (d, J=1.97 Hz, 1H) 8.25 (d, J=1.97 Hz, 1H). 13C NMR (75 MHz, chloroform-d) δ ppm 54.71 (s, 1 C) 113.51 (s, 1 C) 118.90 (s, 1 C) 125.53 (s, 1 C) 140.63 (s, 1 C) 144.40 (s, 1 C) 148.93 (s, 1 C).

後処理

  1. customfitted with an inert atmosphere inlet
  2. customfor 3 h
  3. temperaturecooled
  4. filtrationThe slurry was filtered through a 0.22 μm PTFE
  5. filtrationfilter
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified in one injection
  8. washA fraction that eluted from 10.0 to 11.8 minutes
  9. customwas isolated
  10. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-a8c0c00ae3e74257b1c198a667612f76
出典データセット
uspto-grants-2011_04
特許番号
US07928140B2

反応ノート

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