Trifluoroacetic anhydride → 3-Bromo-2-chloro-6-methylpyridin-1-ium-1-olate

HRID 2196409

反応式

HRID 2196409 の反応式
[Br:1][C:2]1[C:3]([Cl:9])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.OO.NC(N)=[O:14].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:9])=[N+:4]([O-:14])[C:5]([CH3:8])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 27344183-Bromo-2-chloro-6-methylpyridine

生成物 1

HCID 857064893-Bromo-2-chloro-6-methylpyridin-1-ium-1-olate収率 102.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of 3-bromo-2-chloro-6-methylpyridine (1 g, 4.84 mmol) and urea hydrogen peroxide (911 mg, 9.69 mmol) in DCM (24 mL) at 0° C. was added trifluoroacetic anhydride (1.4 mL, 9.69 mmol). After warming to 25° C. over 12 h, the solution was partitioned between H2O-DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (silica, 1% MeOH in DCM) yielding the title compound (1.1 g, quant.) as a white solid: LCMS (ES) m/z=223 (M+H)+.

後処理

  1. customthe solution was partitioned between H2O-DCM
  2. washThe aqueous phase was washed several times with DCM
  3. dry with materialthe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified via column chromatography (silica, 1% MeOH in DCM)

出典と根拠

ORDレコード
ord-f0377ca4ecf94504b22964cc4b9605f3
出典データセット
uspto-grants-2012_12
特許番号
US08338434B2

関連ノート

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