Tetrahydrofuran → 4-(2-bromopropanoyl)phenyl benzoate

HRID 2217788Notes

Reaction equation

HRID 2217788 reaction equation
O1CCCC1.[C:6]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:24])[CH2:22][CH3:23])=[CH:17][CH:16]=1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:25]Br.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CCCCCC>[C:6]([O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21](=[O:24])[CH:22]([Br:25])[CH3:23])=[CH:19][CH:20]=1)(=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24408BromineHCID 241628HCID 241628, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 2703994-(2-bromopropanoyl)phenyl benzoateYield 80%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (30 mL) of 3.00 g (11.9 mmol) of the p-(benzoyloxy)propiophenone, a hexane solution (5 mL) of 2.07 g (1.1 equivalents) of bromine was added at 5° C. The temperature of the mixture was elevated to room temperature, followed by 1 hour of stirring. To the resulting mixture, 30 mL of a saturated sodium hydrogen carbonate solution and 40 mL of ethyl acetate were added to conduct extraction. The organic layer was washed with 30 mL of a saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and subjected to distillation under a reduced pressure to remove the solvents. An yellow oily substance (5.54 g) was obtained as a result. This substance was crystallized from 5 mL of ethyl acetate and 30 mL of hexane. White crystals of 1-[4-(benzoyloxy)phenyl]-2-bromo-1-propanone were obtained as a result (3.147 g, isolation yield: 80%).

Workup

  1. customwas elevated to room temperature
  2. extractionextraction
  3. washThe organic layer was washed with 30 mL of a saturated sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationsubjected to distillation under a reduced pressure
  6. customto remove the solvents
  7. customAn yellow oily substance (5.54 g) was obtained as a result
  8. customThis substance was crystallized from 5 mL of ethyl acetate and 30 mL of hexane

Sources & evidence

ORD record
ord-bf81ddf58e6d46e088340d8317d7c1a6
Source dataset
uspto-grants-2008_08
Patent number
US07408084B2

Reaction notes

Loading…