Water → 5-Bromo-3-methylpyridine-2-carbonitrile

HRID 2357527

反応式

HRID 2357527 の反応式
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[Cu][C:11]#[N:12].O>CN(C=O)C>[Br:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([C:11]#[N:12])=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 962WaterHCID 8176802,5-Dibromo-3-methylpyridineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 207750075-Bromo-3-methylpyridine-2-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
115 °C

実験手順

A mixture of 2,5-dibromo-3-methylpyridine (20.17 g, 80.4 mmol) and copper(I) cyanide (7.24 g, 80.8 mmol) in 200 mL DMF was heated to 115° C. overnight. The reaction mixture was cooled to 25° C. and poured into 600 mL of H2O. The solid was filtered, washed with copious amounts of H2O. The filtrate was extracted with EtOAc (4×) and the combined organic layers were washed with H2O and dried over Na2SO4. The solution was filtered, evaporated onto silica gel and purified by flash chromatography eluting with EtOAc:hexane (0:1→1:9) to give the title compound as a white solid. MS m/z: 197.0 [M+1].

後処理

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. filtrationThe solid was filtered
  3. washwashed with copious amounts of H2O
  4. extractionThe filtrate was extracted with EtOAc (4×)
  5. washthe combined organic layers were washed with H2O
  6. dry with materialdried over Na2SO4
  7. filtrationThe solution was filtered
  8. customevaporated onto silica gel
  9. custompurified by flash chromatography
  10. washeluting with EtOAc:hexane (0:1→1:9)

出典と根拠

ORDレコード
ord-13b02afa25e044f4afc5c246dbf84619
出典データセット
uspto-grants-2010_07
特許番号
US07759337B2

関連ノート

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