Acetic Acid → 1-Benzyl-4-(benzyloxy)-3-bromo-6-methylpyridin-2(1h)-one

HRID 1866869Notes

Reaction equation

HRID 1866869 reaction equation
[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:10][C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C([O-])(=O)C.[Na+].[Br:33]Br>O>[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]([Br:33])[C:9]1=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 517045Sodium AcetateHCID 101495921-benzyl-4-(benzyloxy)-6-methylpyridin-2(1H)-one2×

Product 1

HCID 101727461-Benzyl-4-(benzyloxy)-3-bromo-6-methylpyridin-2(1h)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product from example 35, 1-benzyl-4-(benzyloxy)-6-methylpyridin-2(1H)-one (4.2 mmol, 1.3 g), acetic acid (50 mL), and sodium acetate (5.0 mmol, 0.41 g) were stirred at room temperature. Bromine (4.2 mmol, 0.67 g) was added drop wise with stirring. After ½ hour, water (100 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and brine. After drying over magnesium sulfate and concentrating, the mixture was purified by flash column chromatography eluting with ethyl acetate:hexanes (1:2). The appropriate fractions were concentrated to yield a light oil. (1.0 g, 62%): 1H NMR (DMSO-d6/300 MHz) 7.4-7.0 (m, 10H), 6.5 (s, 1H), 5.29 (s, 2H), 5.27 (s, 2H), 2.2 (s, 3H). ESHRMS m/z 384.057 (M+H, C20H18NO2Br requires 384.060).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialAfter drying over magnesium sulfate
  4. concentrationconcentrating
  5. customthe mixture was purified by flash column chromatography
  6. washeluting with ethyl acetate:hexanes (1:2)
  7. concentrationThe appropriate fractions were concentrated
  8. customto yield a light oil

Sources & evidence

ORD record
ord-ba580240c7464dd09dc9e3cb1e5369a8
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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