Bromine → 2-Bromo-1-(3-chlorophenyl)-3-(4-chlorophenyl)propan-1-one

HRID 63922Notes

Reaction equation

HRID 63922 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:18])[CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Br:19]Br>CC(O)=O>[Br:19][CH:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:18]

Participants

4

Reactant 2

HCID 24408BromineHCID 247260821-(3-Chlorophenyl)-3-(4-chlorophenyl)propan-1-one

Product 1

HCID 1188630992-Bromo-1-(3-chlorophenyl)-3-(4-chlorophenyl)propan-1-oneYield 20%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-(3-chlorophenyl)-3-(4-chlorophenyl)propan-1-one (1.39 g, 5 mmol) in HOAc (15 mL) at 0° C. was added Br2 (800 mg, 5 mmol) dropwise. The reaction was refluxed for 8 h, cooled to RT, concentrated then diluted with EA (25 mL) and water (5 mL). The organic layer was washed with brine (5 mL), dried over Na2SO4 and concentrated to give a residue which was purified by chromatography eluted with PE/EA (50:1) to give 2-bromo-1-(3-chlorophenyl)-3-(4-chlorophenyl)propan-1-one (358 mg, 20% yield) as a brown solid. LCMS: MH+ 359 and TR=2.029 min.

Workup

  1. temperatureThe reaction was refluxed for 8 h
  2. concentrationconcentrated
  3. additionthen diluted with EA (25 mL) and water (5 mL)
  4. washThe organic layer was washed with brine (5 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give a residue which
  8. customwas purified by chromatography
  9. washeluted with PE/EA (50:1)

Sources & evidence

ORD record
ord-e7e85e60e6ae49eabf11c4b8a76c5faf
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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