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

HRID 1436182Notes

Reaction equation

HRID 1436182 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-a023bb6c39a64614b3b6021ad6f33adb
Source dataset
uspto-grants-2009_11
Patent number
US07618981B2

Reaction notes

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