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

HRID 747925Notes

Reaction equation

HRID 747925 reaction equation
[Br:1]Br.[I:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1>C(O)(=O)C>[Br:1][CH2:11][C:10]([C:7]1[CH:8]=[CH:9][C:4]([I:3])=[CH:5][CH:6]=1)=[O:12]

Participants

4

Reactant 2

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

Product 1

HCID 2565722-Bromo-1-(4-iodophenyl)ethanoneYield 93.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (79.3 g, 508 mmo) in glacial acetic acid (50 mL) was added at room temperature to a solution of 1-(4-Iodo-phenyl)-ethanone (Aldrich, 125 g, 508 mmol) in glacial acetic acid (600 mL). The mixture was stirred for 10 h, then concentrated under reduced pressure and the residue was diluted with ethyl acetate (100 mL), and washed with brine (3×50 mL). The organic layer was concentrated, and the residue was crystallized from ethyl ether to provide the title compound as a yellow solid (150 g, 462 mmol, 91% yield). 1H NMR (300 MHz, CDCl3) δ 4.39 (s, 2H), 7.69 (d, J=8.5 Hz, 2H), 7.87 ppm (d, J=8.5 Hz, 2H); MS (DCl/NH3) m/z 246 (M—Br)+264 (M—Br+NH4)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (100 mL)
  3. washwashed with brine (3×50 mL)
  4. concentrationThe organic layer was concentrated
  5. customthe residue was crystallized from ethyl ether

Sources & evidence

ORD record
ord-b1304cf59f0148bfbd9e62c447c7be85
Source dataset
uspto-grants-2008_07
Patent number
US07399765B2

Reaction notes

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