Bromine → 3-bromo-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one

HRID 1866898

Reaction equation

HRID 1866898 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][NH:9][C:8](=[O:12])[CH:7]=1.[Br:18]Br>CC(O)=O>[Br:18][C:7]1[C:8](=[O:12])[NH:9][CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 220503904-(2,4-difluorobenzyloxy)-1H-pyridin-2-one

Product 1

HCID 220508323-bromo-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-oneYield 102.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To an ice-cold solution of 4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one (0.75 g, 3.1 mmol) in AcOH (12 mL) was added a solution of bromine (0.2 mL, 3.5 mmol) in AcOH (6 mL), and the reaction mixture was stirred 10 min. The solvent was removed under reduced pressure to afford 3-bromo-4-(2,4-difluorobenzyloxy)-1H-pyridin-2-one as a white solid (1.0 g, 100%): ESI MS m/z 299 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6152d301c3d547dda88e0ab9fbfb0c8d
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Linked notes

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