1-(5-Bromo-2-nitrophenyl)ethan-1-ol → 1-(5-Bromo-2-nitrophenyl)ethanone

HRID 2423518Notes

Reaction equation

HRID 2423518 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[Br:14][C:15]1[CH:16]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]([CH:21]([OH:23])[CH3:22])[CH:20]=1>CC(C)=O>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]([C:21](=[O:23])[CH3:22])[CH:20]=1

Participants

4

Reactant 2

HCID 450733901-(5-Bromo-2-nitrophenyl)ethan-1-olHCID 131709961Jones' reagent

Product 1

HCID 122241571-(5-Bromo-2-nitrophenyl)ethanoneYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones Reagent (2.67 M, 2.54 mL, 6.79 mmol) was added dropwise to 1-(5-bromo-2-nitrophenyl)-ethanol (1.67 g, 6.79 mmol) in acetone (34 mL) at 0° C., then the reaction mixture was stirred for 10 minutes. Any excess Jones reagent was quenched by the addition of iso-propanol, then the reaction mixture was neutralized with saturated sodium bicarbonate, and the acetone was removed by evaporation. Water was added and the solution was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:9 ethyl acetate:hexanes to give 1.27 g (77%) of 1-(5-bromo-2-nitrophenyl)-ethanone as a solid. 1H NMR (400 MHz, d6-DMSO): δ 8.05 (d, J=5 Hz, 1H), 8.04 (s, 1H), 7.96 (dd, J=9, 2 Hz, 1H), 2.57 (s, 3H).

Workup

  1. customAny excess Jones reagent was quenched by the addition of iso-propanol
  2. customthe acetone was removed by evaporation
  3. additionWater was added
  4. extractionthe solution was extracted with diethyl ether
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 1:9 ethyl acetate

Sources & evidence

ORD record
ord-65099191847e4dec8488c819bda6cb39
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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