2-Bromoanisole → Benzophenone

HRID 1404823Notes

Reaction equation

HRID 1404823 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1OC.[Cl-].[Al+3].[Cl-].[Cl-].CO[C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20]>ClCCl>[C:19]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:20])[C:18]1[CH:22]=[CH:23][CH:24]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 113582-BromoanisoleHCID 74374m-Anisoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3102Benzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

60.6 g (324.2 mmol) of 2-bromoanisole was added dropwise to a dichloromethane (350 ml) solution containing 51.8 g (388.6 mmol) of aluminum chloride and 55.31 g (324.3 mmol) of 3-methoxybenzoyl chloride which was cooled to 0° C. After addition, the resulting mixture was stirred for 2 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 (47) as 67.7 g (210.7 mmol, yield of 65%) of a yellow solid.

Workup

  1. additionAfter addition
  2. customAfter a reaction
  3. washthe reaction solution was washed with water
  4. customthe solvent was removed
  5. customthe obtained product was purified by column chromatography

Sources & evidence

ORD record
ord-5451d1f1aca646d380479eeab2366adf
Source dataset
uspto-grants-2014_12
Patent number
US08916071B2

Reaction notes

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