Bromine → 2-Bromo-1-(4-bromo-2-fluorophenyl)ethanone

HRID 2114388Notes

Reaction equation

HRID 2114388 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([F:11])[CH:3]=1.[Br:12]Br>C(Cl)(Cl)Cl>[Br:12][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:11])=[O:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 219385811-(4-Bromo-2-fluorophenyl)ethan-1-one

Product 1

HCID 221214832-Bromo-1-(4-bromo-2-fluorophenyl)ethanoneYield 89.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

1-(4-Bromo-2-fluorophenyl)ethanone (2.59 g, 11.9 mmol, 1.00 equiv) was dissolved in chloroform (5 mL) and cooled to 5° C. Bromine (0.613 mL, 11.9 mmol, 1.00 equiv) was added dropwise via syringe. On completion of the addition, the bath was removed and the reaction was allowed to warm to room temperature. After two hours, the reaction was poured onto ice and diluted with EtOAc. The mixture was washed sequentially with saturated NaHCO3, water, and saturated NaCl. The organic phase was dried over Na2SO4, filtered and concentrated to afford 3.14 g (89%) of a white solid. 1H NMR (CDCl3) 7.92-7.83 (m, 1H), 7.51-40 (m, 2H), 4.50 (s, 2H).

Workup

  1. additionOn completion of the addition
  2. customthe bath was removed
  3. temperatureto warm to room temperature
  4. additionthe reaction was poured onto ice
  5. additiondiluted with EtOAc
  6. washThe mixture was washed sequentially with saturated NaHCO3, water, and saturated NaCl
  7. dry with materialThe organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1c2fa2f7af05438492838499a2671fae
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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