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

HRID 1890447Notes

Reaction equation

HRID 1890447 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 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 the 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 aluminum 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 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 brine. 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 the 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 1-5° C.
  8. additionpoured onto ice
  9. customThe organic phase is separated
  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 brine
  12. customThen the organic phase is dried
  13. customthe solvent is removed
  14. customthe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-b2568bb9ef2b49feb814c41bbaf73354
Source dataset
uspto-grants-2013_08
Patent number
US08507450B2

Reaction notes

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