Bromine → 2-Bromo-1-(4-iodophenyl)ethanone

HRID 970013Notes

Reaction equation

HRID 970013 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[Br:11]Br>C(O)(=O)C>[Br:11][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)=[O:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 728691-(4-Iodophenyl)ethan-1-one

Product 1

HCID 2565722-Bromo-1-(4-iodophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To the solution of 1-(4-Iodo-phenyl)-ethanone (Aldrich, 125 g, 508 mmol) in glacial acetic acid (600 mL) was added the bromine (Aldrich, 79.3 g, 508 mmol, in 50 mL of acetic acid) and stirred at room temperature for 10 hours. It was concentrated under reduced pressure. The residue was then diluted with ethyl acetate (100 mL) and washed with brine (3×50 mL). The organic solution was concentrated. The title compound was obtained as yellow solid by recrystallization from diethyl ether (150 g, 91%). 1H NMR (300 MHz, CDCl3) δ 4.39 (s, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.87 (d, J=8.5 Hz, 2 H) ppm; MS (DCl/NH3) m/z 246 (M−Br)+, 264 (M−Br+NH4)+.

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. additionThe residue was then diluted with ethyl acetate (100 mL)
  3. washwashed with brine (3×50 mL)
  4. concentrationThe organic solution was concentrated

Sources & evidence

ORD record
ord-97d5fc8c42fb46f0ac7c1bf2bf5e0282
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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