Boron tribromide → 5-Bromo-3-hydroxy-1-methyl-1,2-dihydropyridin-2-one

HRID 518495Notes

Reaction equation

HRID 518495 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10]C)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 1016677185-Bromo-3-methoxy-1-methyl-1,2-dihydropyridin-2-one

Product 1

HCID 840489365-Bromo-3-hydroxy-1-methyl-1,2-dihydropyridin-2-oneYield 57.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-3-methoxy-1-methylpyridin-2-one (5.60 g, 25.7 mmol) stirred at 0° C. in DCM (100 mL) was added BBr3 (12.87 g, 51.4 mmol). The icebath was removed and the mixture was stirred at rt for 5 h. After the mixture was cooled to 0° C., it was quenched with MeOH (5 mL), concentrated to near dryness and purified by column chromatography on silica gel to give title compound (3 g, 57%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.49 (s, 1H), 6.80 (s, 1H), 3.44 (s, 3H). LCMS (M+H)+=205.

Workup

  1. customThe icebath was removed
  2. temperatureAfter the mixture was cooled to 0° C.
  3. customit was quenched with MeOH (5 mL)
  4. concentrationconcentrated
  5. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-df1284f6688f4c9dbb782b076970bc36
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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