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

HRID 1697805Notes

Reaction equation

HRID 1697805 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>O1CCOCC1>[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 312751,4-DioxaneSolvent

Procedure

A solution of 1-(4-iodophenyl)ethanone (55.9 mmol) in dioxane (160 mL) was cooled to 10° C. Bromine (1.1 equiv, 61.6 mmol) was added dropwise to the reaction mixture. After 10 min, the cooling bath was removed and the reaction mixture was stirred at room temperature. After 1.5 h, the reaction mixture was concentrated in vacuo, poured into water (100 mL), and extracted with (3×100 mL) ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to a tan solid (18.2 g) which was used directly in the next step.

Workup

  1. customthe cooling bath was removed
  2. waitAfter 1.5 h
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additionpoured into water (100 mL)
  5. extractionextracted with (3×100 mL) ethyl acetate
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated in vacuo to a tan solid (18.2 g) which

Sources & evidence

ORD record
ord-717c39e947e04de5a7919287d731880e
Source dataset
uspto-grants-2012_04
Patent number
US08163919B2

Reaction notes

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