N-methyl-2-pyrrolidone → 4-(Benzyloxy)-2-fluorobenzonitrile

HRID 433047ノート

反応式

HRID 433047 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[C:11]([F:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][N:18]1CCCC1=O>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:17]#[N:18])=[C:11]([F:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

3

反応物 2

HCID 13387N-methyl-2-pyrrolidoneHCID 222739334-(Benzyloxy)-1-bromo-2-fluorobenzene

生成物 1

HCID 113336284-(Benzyloxy)-2-fluorobenzonitrile

実験手順

Compound 20 (10.00 g, 35.7 mmol) and cuprous cyanide (13.00 , 71.4 mmol) were suspended in 1-methyl-2-pyrollidinone (250 ml) and heated under reflux for 24 h. The reaction mixture was cooled to room temperature and filtered through ‘hyflo’ to remove the excess cuprous cyanide. Water (200 ml) was added to the solution which was subsequently washed with ether (2×400 ml). The combined ether extracts were then washed with water (2×500 ml) and brine (500 ml) and then dried (MgSO4). The drying agent was filtered off and the solvent removed in vacuo to yield an off-white solid which was purified by column chromatography (dichloromethane) on silica to yield colourless crystals. Yield 5.79 g (71%).

後処理

  1. temperatureheated
  2. temperatureunder reflux for 24 h
  3. filtrationfiltered through ‘hyflo’
  4. customto remove the excess cuprous cyanide
  5. additionWater (200 ml) was added to the solution which
  6. washwas subsequently washed with ether (2×400 ml)
  7. washThe combined ether extracts were then washed with water (2×500 ml) and brine (500 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationThe drying agent was filtered off
  10. customthe solvent removed in vacuo
  11. customto yield an off-white solid which
  12. customwas purified by column chromatography (dichloromethane) on silica
  13. customto yield colourless crystals

出典と根拠

ORDレコード
ord-da16493528ee4dbe872a115cfbfbdd48
出典データセット
uspto-grants-2003_12
特許番号
US06666989B1

反応ノート

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