Water → 5-Bromo-6-methylpyridine-2-carbonitrile

HRID 632201ノート

反応式

HRID 632201 の反応式
[C-:1]#[N:2].[Na+].[Br:4][C:5]1[C:6]([CH3:12])=[N:7][C:8](F)=[CH:9][CH:10]=1.O>CS(C)=O>[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C:1]#[N:2])=[N:7][C:6]=1[CH3:12]

参加物

5

反応物 3

HCID 962WaterHCID 8929Sodium CyanideHCID 177501493-Bromo-6-fluoro-2-methylpyridine

生成物 1

HCID 498187795-Bromo-6-methylpyridine-2-carbonitrile収率 15%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

NaCN (4 g, 82 mmol) was added to a solution of 3-bromo-6-fluoro-2-methyl-pyridine (4 g, 21 mmol) in DMSO (100 mL) The mixture was stirred for 2 h at 100° C., poured into H2O (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were dried over Na2SO4, concentrated and purified by flash column chromatography (silica gel, 10 g, eluting with 10% ethyl acetate in petroleum ether) to give the title compound (0.6 g, 15%) as white solid; MS (D): m/e=197.0 [M+H]+.

後処理

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. dry with materialThe organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (silica gel, 10 g, eluting with 10% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-c6368b07588c4bb28e4e77e752f070ac
出典データセット
uspto-grants-2016_04
特許番号
US09321727B2

反応ノート

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