Dimethylformamide → (5-Bromo-2-chloro-phenyl)-(4-ethoxy-phenyl)-methanone

HRID 2263584Notes

Reaction equation

HRID 2263584 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=O.CN(C)[CH:9]=[O:10].[Br:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:22])=[C:17]([CH:21]=1)[C:18]([OH:20])=O>ClCCl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:22])=[C:17]([C:18]([C:2]2[CH:1]=[CH:17][C:21]([O:10][CH3:9])=[CH:13][CH:14]=2)=[O:20])[CH:21]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 331275-Bromo-2-chlorobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 22328608(5-Bromo-2-chloro-phenyl)-(4-ethoxy-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

38.3 ml oxalyl chloride and 0.8 ml of dimethylformamide are added to a mixture of 100 g of 5-bromo-2-chloro-benzoic acid in 500 ml dichloromethane. The reaction mixture is stirred for 14 h, then filtered and separated from all volatile constituents in rotary evaporator. The residue is dissolved in 150 ml dichloromethane, the solution is cooled to −5° C., and 46.5 g of anisole are added. Then 51.5 g of aluminium trichloride are added batchwise so that the temperature does not exceed 5° C. The solution is stirred for another 1 h at 1-5° C. and then poured onto ice. The organic phase is separated off and the aqueous phase is extracted another three times with dichloromethane. The combined organic phases are washed with aqueous 1 M hydrochloric acid, twice with 1 M sodium hydroxide solution and with saturated sodium chloride solution. Then the organic phase is dried, the solvent is removed and the residue is recrystallised from ethanol.

Workup

  1. filtrationfiltered
  2. customseparated from all volatile constituents in rotary evaporator
  3. dissolutionThe residue is dissolved in 150 ml dichloromethane
  4. addition46.5 g of anisole are added
  5. additionThen 51.5 g of aluminium trichloride are added batchwise so that the temperature
  6. customdoes not exceed 5° C
  7. stirringThe solution is stirred for another 1 h at 1-5° C.
  8. additionpoured onto ice
  9. customThe organic phase is separated off
  10. extractionthe aqueous phase is extracted another three times with dichloromethane
  11. washThe combined organic phases are washed with aqueous 1 M hydrochloric acid, twice with 1 M sodium hydroxide solution and with saturated sodium chloride solution
  12. customThen the organic phase is dried
  13. customthe solvent is removed
  14. customthe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-def4600d437c462f8ff229b93359dbfe
Source dataset
uspto-grants-2010_12
Patent number
US07851602B2

Reaction notes

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