Sodium Bicarbonate → (3-Bromo-phenyl)-(2,4-dichloro-pyrimidin-5-yl)-methanone

HRID 1809705ノート

反応式

HRID 1809705 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[C:11]([Cl:17])=[N:12][C:13]([Cl:16])=[N:14][CH:15]=2)[OH:9])[CH:5]=[CH:6][CH:7]=1.C([O-])(O)=O.[Na+].CC1(C)N([O])C(C)(C)CCC1.[O-]Cl.[Na+]>ClCCl.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:11]([Cl:17])=[N:12][C:13]([Cl:16])=[N:14][CH:15]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 516892Sodium BicarbonateHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 86667962(3-Bromo-phenyl)-(2,4-dichloro-pyrimidin-5-yl)-methanol

生成物 1

HCID 86667963(3-Bromo-phenyl)-(2,4-dichloro-pyrimidin-5-yl)-methanone

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To the solution of (3-bromo-phenyl)-(2,4-dichloro-pyrimidin-5-yl)-methanol (from Example 36 supra) (33 g, 0.098 mol) in dichloromethane (300 mL) was added water (30 mL), NaHCO3 (3.8 g, 0.045 mol), TEMPO (156 mg, 1 mmol) and Bu4NI (1 g, 2.7 mmol) successively. The mixture was cooled to 0° C. and then aqueous NaClO (146 mL) was added dropwise. The resulting mixture was stirred for another two hours. The organic phase was separated and washed with water (100 mL), brine (100 mL) and dried over Na2SO4. The drying agent was removed by filtration and the residue was evaporated to give crude (3-bromo-phenyl)-(2,4-dichloro-pyrimidin-5-yl)-methanone as yellow solid. (Yield 30.2 g, 92%).

後処理

  1. customThe organic phase was separated
  2. washwashed with water (100 mL), brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. customThe drying agent was removed by filtration
  5. customthe residue was evaporated

出典と根拠

ORDレコード
ord-d2fdd85492f741f2a52c18e84bf04e05
出典データセット
uspto-grants-2013_01
特許番号
US08362023B2

反応ノート

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