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

HRID 1782199Notes

Reaction equation

HRID 1782199 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. Water (200 mL) was added to the residue, 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, filtered and 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. additionWater (200 mL) was added to the residue
  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. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c26e4473b77647adb7f608be14a477d3
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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