Tetrahydrofuran → 2-Bromo-1-phenylbutan-1-one

HRID 2217785Notes

Reaction equation

HRID 2217785 reaction equation
O1CCCC1.[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])[CH2:7][CH2:8][CH3:9].CCCCCC.[Br:23]Br>C(OCC)(=O)C.O>[C:11]1([C:6](=[O:10])[CH:7]([Br:23])[CH2:8][CH3:9])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 10315ButyrophenoneHCID 24408Bromine

Product 1

HCID 526962-Bromo-1-phenylbutan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (20 mL) of 9.917 g (67.0 mmol) of butyrophenone, a hexane solution (10 mL) of 11.78 g (1.1 equivalents) of bromine was gradually added at 5° C. The temperature was elevated to 15° C., and the solution was stirred for 1 hour. To the solution, 20 mL of water 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 three times, dried over anhydrous magnesium sulfate, and subjected to distillation under a reduced pressure to remove the solvents. 1-Phenyl-2-bromo-1-butanone was obtained as a light peach-colored oily substance (23.94 g, crude yield: 92%).

Workup

  1. customwas elevated to 15° C.
  2. extractionextraction
  3. washThe organic layer was washed with 30 mL of a saturated sodium hydrogen carbonate solution three times
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationsubjected to distillation under a reduced pressure
  6. customto remove the solvents

Sources & evidence

ORD record
ord-27c45f464afc43e0b416843672e60113
Source dataset
uspto-grants-2008_08
Patent number
US07408084B2

Reaction notes

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