4-Ethylbenzoyl chloride → (5-Bromo-2-chloro-4-methoxyphenyl)(4-ethylphenyl)methanone

HRID 1713588Notes

Reaction equation

HRID 1713588 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH3:10].[CH2:11]([C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)[CH3:12].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[CH:4][C:5]([Cl:8])=[C:6]([C:17]([C:16]2[CH:20]=[CH:21][C:13]([CH2:11][CH3:12])=[CH:14][CH:15]=2)=[O:18])[CH:7]=1

Participants

5

Reactant 3

HCID 853684-Ethylbenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 179848451-Bromo-4-chloro-2-methoxybenzene

Product 1

HCID 46206796(5-Bromo-2-chloro-4-methoxyphenyl)(4-ethylphenyl)methanoneYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-bromo-4-chloro-2-methoxybenzene (5.1 g, 23 mmol) and 4-ethylbenzoyl chloride (4.1 g, 24 mmol) in 15 mL of anhydrous dichloromethane (DCM) was added aluminum trichloride (3.2 g, 24 mmol). The mixture was stirred at room temperature for 1 hour, followed by heating at reflux for 18 hours. The mixture was poured into 100 mL of ice-cold water and the organic layer was isolated. The aqueous solution was extracted with 25 mL DCM. The combined organic extracts were washed with brine (25 mL), dried (Na2SO4), filtered, and evaporated. Recrystallization from petroleum ether gave the intermediate (5-bromo-2-chloro-4-methoxyphenyl)(4-ethylphenyl)methanone 21 (5.6 g, 69%).

Workup

  1. temperatureby heating
  2. temperatureat reflux for 18 hours
  3. customthe organic layer was isolated
  4. extractionThe aqueous solution was extracted with 25 mL DCM
  5. washThe combined organic extracts were washed with brine (25 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-cd0845e4fd6648d1b4fad80496a26f96
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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