Bromine → 3-Bromo-1-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)-1h-pyridin-2-one

HRID 1831941Notes

Reaction equation

HRID 1831941 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[CH:8][C:7]1=[O:21].[Br:25]Br>CC(O)=O>[Br:25][C:8]1[C:7](=[O:21])[N:6]([CH2:5][C:4]2[CH:22]=[CH:23][CH:24]=[C:2]([F:1])[CH:3]=2)[CH:11]=[CH:10][C:9]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 22049898HCID 22049898, compound

Product 1

HCID 113956343-Bromo-1-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)-1h-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To an ice-cold solution of 1-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)-1H-pyridin-2-one (0.14 g, 0.43 mmol) in AcOH (2 mL) was added a solution of bromine (72 mg, 0.45 mmol) in AcOH (1 mL), and the reaction mixture was stirred for 5 min. The reaction mixture was warmed to room temperature and the solvent was removed under reduced pressure. 1H NMR (300 MHz, CDCl3) δ 7.45-6.95 (m, 9H), 6.05 (d, J=8 Hz, 1H), 5.21 (s, 2H), 5.14 (s, 2H). ES HRMS m/z 406.0254 (M+H C19H15BrF2NO2 requires 406.0249).

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c65dc940e9474ff0932247184bfb22c1
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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