Iodine → Benzophenone

HRID 1404822Notes

Reaction equation

HRID 1404822 reaction equation
II.Br[C:4]1[CH:9]=[CH:8][C:7](Cl)=[C:6](OCC)[CH:5]=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:14]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 807IodineHCID 7412Benzoyl chlorideHCID 509981874-Bromo-1-chloro-2-ethoxybenzene

Product 1

HCID 3102Benzophenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.7 g (357.06 mmol) of Mg and a small amount of iodine were dissolved in 200 ml of THF, and 84.6 g (324.6 mmol) of 1-bromo-4-chloro-3-ethoxybenzene 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. Thereafter, a Grignard reagent containing 50.2 g (357.06 mmol) of benzoyl chloride was added dropwise to the obtained product 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 (42) as 29.6 g (113.6 mmol, yield of 35%) 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-528072fb6fdb4f9b97e8e7768e3b63ef
Source dataset
uspto-grants-2014_12
Patent number
US08916071B2

Reaction notes

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