Benzyl Alcohol → 4-(Benzyloxy)-2-bromonicotinonitrile

HRID 587623ノート

反応式

HRID 587623 の反応式
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][C:12]1[N:19]=[CH:18][CH:17]=[C:16](Br)[C:13]=1[C:14]#[N:15]>CN(C=O)C>[CH2:3]([O:10][C:16]1[C:13]([C:14]#[N:15])=[C:12]([Br:11])[N:19]=[CH:18][CH:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 574595912,4-Dibromopyridine-3-carbonitrile

生成物 1

HCID 230886954-(Benzyloxy)-2-bromonicotinonitrile収率 83.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a suspension of NaH (1.756 g, 45.818 mmol, mineral oil 60%) in DMF (200 ml) cooled at 0° C., was added benzyl alcohol (4.542 g, 42 mmol). The resulting mixture was stirred for 5 min. Then compound D1 (10 g, 38.18 mmol) was quickly added. The resulting reaction mixture was gradually warmed to r.t. and stirred for 1 h. The reaction mixture was quenched with NH4Cl (aqueous sat. solution), diluted with H2O and the resulting mixture was extracted with Et2O. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 1% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D2 (9.2 g, 83%).

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas gradually warmed to r.t.
  3. stirringstirred for 1 h
  4. customThe reaction mixture was quenched with NH4Cl (aqueous sat. solution)
  5. additiondiluted with H2O
  6. extractionthe resulting mixture was extracted with Et2O
  7. customThe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 1% as eluent)
  11. customThe desired fractions were collected
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c162d6edbb1b4c80a4a0cb9547a0fcf0
出典データセット
uspto-grants-2016_01
特許番号
US09226930B2

反応ノート

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