Bromine → alpha-Bromo-3-chloropropiophenone

HRID 1250185Notes

Reaction equation

HRID 1250185 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:11])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[Br:12]Br>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:11])[CH:9]([Br:12])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 5871283'-Chloropropiophenone

Product 1

HCID 4992116alpha-Bromo-3-chloropropiophenoneYield 98.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3′-chloropropiophenone (50.0 g, 297 mmol) in acetonitrile (595 mL) was added bromine (16.67 mL, 327 mmol) at room temperature. The reddish-yellow solution was allowed to stir for 18 h at room temperature. The solution was concentrated in vacuo to provide a reddish solid. The crude material was dissolved in 400 mL of ethyl acetate and washed with 400 mL of water. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give 72.6 g (98%) of crude product. 1H NMR (CDCl3) δ1.90 (d, J=6 Hz, 3H), 5.21 (q, J=6 Hz, 1H), 7.37-7.88 (m, 3H), 7.98 (s, 1H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto provide a reddish solid
  3. washwashed with 400 mL of water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61607cff8c57460aa0d0f8dd1e36c217
Source dataset
uspto-grants-2002_01
Patent number
US06337328B1

Reaction notes

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