Iodine → Benzophenone

HRID 1404818Notes

Reaction equation

HRID 1404818 reaction equation
II.Br[C:4]1[CH:5]=[CH:6][C:7](Cl)=[C:8](OC)[CH:9]=1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[C:13]([C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:9]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 807IodineHCID 7412Benzoyl chlorideHCID 27695675-Bromo-2-chloroanisole

Product 1

HCID 3102Benzophenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After 8.7 g (357.06 mmol) of Mg and a small amount of iodine were dissolved in 200 ml of THF, 71.9 g (324.6 mmol) of 5-bromo-2-chloroanisole dissolved in 500 ml of THF was added dropwise to the resulting solution. After addition, the resulting mixture was refluxed for 3 hours to prepare a Grignard reagent which was then cooled to room temperature. After that, the prepared Grignard reagent was added dropwise to 50.2 g (357.06 mmol) of benzoyl chloride and stirred for 5 hours. After a reaction, the reaction solution was washed with water, the solvent was removed, and the obtained product was purified by column chromatography to obtain a benzophenone derivative represented by the following formula (32) as 32.0 g (129.8 mmol, yield of 40%) of a white solid.

Workup

  1. additionwas added dropwise to the resulting solution
  2. additionAfter addition
  3. temperaturethe resulting mixture was refluxed for 3 hours
  4. customAfter a reaction
  5. washthe reaction solution was washed with water
  6. customthe solvent was removed
  7. customthe obtained product was purified by column chromatography

Sources & evidence

ORD record
ord-40e6317a9e2343e7ae72c881dcaf7dc6
Source dataset
uspto-grants-2014_12
Patent number
US08916071B2

Reaction notes

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