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

HRID 1809705노트

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HRID 1809705 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d2fdd85492f741f2a52c18e84bf04e05
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362023B2

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