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

HRID 1809705Notes

Reaction equation

HRID 1809705 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-d2fdd85492f741f2a52c18e84bf04e05
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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