HCID 18408338, compound → HCID 15457076, compound

HRID 1385959Notes

Reaction equation

HRID 1385959 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[C:13]1[C:14](=[O:24])[N:15]([CH3:23])[C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1.B(Br)(Br)Br.ClCCl>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[C:13]1[C:14](=[O:24])[N:15]([CH3:23])[C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 18408338HCID 18408338, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 15457076HCID 15457076, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.3 g (28.6 mmol) of 3-(2-chloro-4-methoxy-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone was dissolved in 150 ml of dichloromethane, and 30 ml (90 mmol) of a 3N boron tribromide/dichloromethane solution was dropwise added thereto under cooling in a dry ice-acetone bath. The temperature was raised to room temperature, followed by stirring for 2 hours. Then, the mixture was poured into ice water and extracted with dichloromethane. The organic layer was washed with water and a saturated sodium hydrogencarbonate aqueous solution and then dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure to obtain 8.0 g (yield: 80%) of the desired product.

Workup

  1. temperatureunder cooling in a dry ice-acetone bath
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium hydrogencarbonate aqueous solution and then dried over anhydrous magnesium sulfate
  5. distillationThe organic layer was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7d46258a41524023b79c21f30d956e66
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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