2,4-Dichlorobenzoyl chloride → 2',4'-Dichlorobutyrophenone

HRID 1825433Notes

Reaction equation

HRID 1825433 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:12]([Mg]Cl)[CH2:13][CH3:14]>C1COCC1.[Cu]I>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](=[O:5])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 178455855HCID 178455855, compound

Product 1

HCID 131756172',4'-Dichlorobutyrophenone

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A mixture of 2,4-dichlorobenzoyl chloride (4.5 g) and copper (I) iodide (200 mg) in dry THF (30 ml) was cooled to −20° C. under argon. Then a solution of n-propyl magnesium chloride (2 M in ether, 11.0 ml) was added dropwise. Ten minutes after addition was complete, the cooling bath was removed and the mixture stirred for 1 hour. Water was carefully added, followed by extraction with toluene. The toluene layer was washed with dilute HCl, water, saturated sodium bicarbonate solution, dried and concentrated in vacuo to give 1-(2,4-dichlorophenyl)butan-1-one (4.0 g).

Workup

  1. additionTen minutes after addition
  2. customthe cooling bath was removed
  3. additionWater was carefully added
  4. extractionfollowed by extraction with toluene
  5. washThe toluene layer was washed with dilute HCl, water, saturated sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-363faea991ec40beb4f43b2452135675
Source dataset
uspto-grants-2006_05
Patent number
US07045519B2

Reaction notes

Loading…