Bromine → 2-Bromo-1-(2-fluorophenyl)propan-1-one

HRID 554204Notes

Reaction equation

HRID 554204 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:11])[CH2:9][CH3:10].[Br:12]Br>C(O)(=O)C>[Br:12][CH:9]([CH3:10])[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 5793991-(2-Fluorophenyl)propan-1-one

Product 1

HCID 221113342-Bromo-1-(2-fluorophenyl)propan-1-oneYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2′-fluoropropiophenone (25.0 g) in acetic acid (250 mL) was slowly added bromine (8.4 mL). The mixture was stirred at room temperature for 3 hr, and concentrated under reduced pressure. To the residue was added water (200 mL), and the mixture was extracted with diisopropyl ether. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (yield 36.8 g, 97%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added water (200 mL)
  3. extractionthe mixture was extracted with diisopropyl ether
  4. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-056bdc7086cd4304bbd10c8510791b87
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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