m-Chloroperbenzoic acid → 3-Bromo-2-chloro-6-methylpyridin-1-ium-1-olate

HRID 559139ノート

反応式

HRID 559139 の反応式
[Br:1][C:2]1[C:3]([Cl:9])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:9])=[N+:4]([O-:18])[C:5]([CH3:8])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 27344183-Bromo-2-chloro-6-methylpyridine

生成物 1

HCID 857064893-Bromo-2-chloro-6-methylpyridin-1-ium-1-olate収率 1,230.1%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
50 °C

実験手順

step a—To a solution of 3-bromo-2-chloro-6-methyl-pyridine (2.0 g, 0.687 mmol) in CHCl3 was added MCPBA (3.3 g, 19.1 mmol) and the resulting solution was heated at 50° C. overnight, The resulted solution was cooled and partitioned between DCM and sat'd. aq. NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (30 to 80% EtOAc) to afford 1.88 g (87%) of 3-bromo-2-chloro-6-methyl-pyridine 1-oxide (52a) as a white solid.

後処理

  1. temperatureThe resulted solution was cooled
  2. custompartitioned between DCM
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with an EtOAc/hexane gradient (30 to 80% EtOAc)

出典と根拠

ORDレコード
ord-9a9ed184c34a4dcab8378a41dd3dc6e1
出典データセット
uspto-grants-2011_11
特許番号
US08063072B2

反応ノート

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