Benzene, 1-fluoro-2-methyl-4-nitro- → 3-Bromo-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

HRID 218512

Reaction equation

HRID 218512 reaction equation
[Br:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[CH3:25]>CS(C)=O.O>[Br:1][C:2]1[C:3](=[O:8])[N:4]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=2[CH3:25])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 8185493-Bromo-2-hydroxypyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 594101573-Bromo-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

44.5 g (280 mmol) of 3-bromopyridin-2(1H)-one are dissolved in 750 ml of anhydrous dimethyl sulfoxide and admixed at room temperature with 33.4 g (298 mmol) of potassium tert-butoxide in portions. The suspension is stirred at this temperature for 1 h, before 38.5 g (280 mmol) of 1-fluoro-2-methyl-4-nitrobenzene are added and the reaction solution is heated to 80° C. for 20 h. It is allowed to cool and diluted cautiously with water. The precipitated crystalline solid is filtered off, washed with a little water and dried under reduced pressure. This affords 62 g (80% of theory) of the desired product.

Workup

  1. additionare added
  2. temperatureto cool
  3. filtrationThe precipitated crystalline solid is filtered off
  4. washwashed with a little water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-095551dc86b244eb93822301a94506b3
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Linked notes

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