Bromine → HCID 22050579, compound

HRID 1831906Notes

Reaction equation

HRID 1831906 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.[Br:17]Br>CC(O)=O>[Br:17][C:9]1[C:10](=[O:14])[NH:11][CH:12]=[CH:13][C:8]=1[O:7][CH2:6][C:5]1[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-one

Product 1

HCID 22050579HCID 22050579, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To an ice-cold solution of 4-(4-fluorobenzyloxy)pyridine-2(1H)-one (3.1 g, 14 mmol) in AcOH (26 mL) was added a solution of bromine (0.79 mL, 15 mmol) in AcOH (51 mL), and the reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure, and purification by flash column chromatography (silica, 1:1 Et2O/hexanes) to afford 3-bromo-4-(4-fluorobenzyloxy)-1H-pyridin-2-one as an orange solid (0.78 g, 48%): MS APCI m/z 298 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure, and purification by flash column chromatography (silica, 1:1 Et2O/hexanes)

Sources & evidence

ORD record
ord-89eff5315ed242a1944f9ba3f431ce8b
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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