Phenacyl bromide → HCID 24215714, compound

HRID 905533Notes

Reaction equation

HRID 905533 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]>CN(C=O)C>[C:14]1([C:12](=[O:13])[CH2:11][O:3][C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 79713-HydroxypyridineHCID 24758Sodium hydride

Product 1

HCID 24215714HCID 24215714, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension NaH (0.8 g, 60%, 20 mmol) in DMF (15 mL) was added a solution of 3-hydroxylpyridine (1.9 g, 20 mmol) in DMF (10 mL) at ° C. under nitrogen. After the mixture was stirred 15 min, a solution of 2-bromoacetophenone (3.98 g, 20 mmol) in DMF (10 mL) was added dropwise. The resulting mixture was stirred for 5 h until the starting material consumed. Water was added to quench the reaction and the aqueous phase was extracted with CH2Cl2 (3×40 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography eluted by hexane:ethyl acetate (1:1) and the correct product was obtained as a white solid; mp 81-82° C.; yield 75% (3.19 g); H NMR (400 MHz, CDCl3): d 5.40 (s, 2H, OCH2), 7.28 (m, 2H, Ar), 7.59 (m, 2H, Ar), 7.67 (m, 1H, Ar), 8.03 (m, 2H, Ar), 8.32 (m, 1H, Ar), 8.43 (m, 1H, Ar); CNMR (100 MHz, CDCl3): δ 70.8, 121.7, 123.9, 128.1, 129.0, 134.2, 134.3, 138.2, 143.1, 154.4, 193.6; IR ν (cm−1) 3054, 3007, 2988, 2963, 2898, 1702, 1579, 1486, 1450, 1422, 1275, 1263, 1233, 1090, 974, 815, 765, 751.

Workup

  1. stirringThe resulting mixture was stirred for 5 h until the starting material
  2. customconsumed
  3. additionWater was added
  4. customto quench
  5. customthe reaction
  6. extractionthe aqueous phase was extracted with CH2Cl2 (3×40 mL)
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash column chromatography
  11. washeluted by hexane:ethyl acetate (1:1)
  12. customthe correct product was obtained as a white solid

Sources & evidence

ORD record
ord-84640d0e0764492aa29db78a9b8e5352
Source dataset
uspto-grants-2011_09
Patent number
US08012901B1

Reaction notes

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