Bromine → HCID 54724177, compound

HRID 1866920Notes

Reaction equation

HRID 1866920 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]1=[O:13].[Br:17]Br>CC(O)=O>[Br:17][C:8]1[C:7](=[O:13])[N:6]([CH2:5][C:4]2[CH:14]=[CH:15][CH:16]=[C:2]([F:1])[CH:3]=2)[CH:11]=[CH:10][C:9]=1[OH:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 54724162HCID 54724162, compound

Product 1

HCID 54724177HCID 54724177, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To an ice-cold solution of 1-(3-fluorobenzyl)-4-hydroxy-1H-pyridin-2-one (0.67 g, 3.1 mmol) in AcOH (5.7 mL) was added a solution of bromine (0.52 g, 3.24 mmol) in AcOH (10.8 mL), and the reaction mixture was stirred for 5 min. The reaction mixture was warmed to room temperature and concentrated under reduced pressure to afford 3-bromo-1-(3-fluorobenzyl)-4-hydroxy-1H-pyridin-2-one as a yellow solid (1.07 g, crude): 1H NMR (500 MHz, MeOD) δ 7.64 (d, J=8 Hz, 1H), 7.35-7.30 (m, 1H), 7.05-6.90 (m, 3H), 6.20 (d, J=8 Hz, 1H), 5.18 (s, 2H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb14a8b3548847eba87abc1d00cc025e
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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