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

HRID 500318Notes

Reaction equation

HRID 500318 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 a rotary evaporator. The residue is dissolved in 150 ml dichloromethane, the resulting solution is cooled to −5° C., and 46.5 g of anisole are added. Then 51.5 g of aluminum trichloride are added batchwise so that the temperature does not exceed 5° C. The solution is stirred for another 1 h at 1 to 5° C. and then poured onto crushed ice. The organic phase is separated, and the aqueous phase is extracted 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 brine. The organic phase is dried, the solvent is removed in vacuo, and the residue is recrystallized from ethanol.

Workup

  1. filtrationfiltered
  2. customseparated from all volatile constituents in a 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 aluminum 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 to 5° C.
  8. additionpoured
  9. customonto crushed ice
  10. customThe organic phase is separated
  11. extractionthe aqueous phase is extracted three times with dichloromethane
  12. washThe combined organic phases are washed with aqueous 1 M hydrochloric acid, twice with 1 M sodium hydroxide solution
  13. customThe organic phase is dried
  14. customthe solvent is removed in vacuo
  15. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-119e7632fe7a487b983c08fbe256a581
Source dataset
uspto-grants-2010_08
Patent number
US07772191B2

Reaction notes

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