5-Bromo-2-chlorobenzoic acid → HCID 67069095, compound

HRID 909786Notes

Reaction equation

HRID 909786 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:17])=[C:12]([CH:16]=1)[C:13]([OH:15])=O.[F:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[O:26][CH2:27][CH3:28].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)(Cl)Cl.O.CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:17])=[C:12]([C:13]([C:23]2[CH:24]=[C:19]([F:18])[C:20]([O:26][CH2:27][CH3:28])=[CH:21][C:22]=2[F:25])=[O:15])[CH:16]=1

Participants

8

Reactant 4

HCID 331275-Bromo-2-chlorobenzoic acidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18726814HCID 18726814, compound

Product 1

HCID 67069095HCID 67069095, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Oxalyl chloride (1.89 mL, 0.0220 mol) and N,N-dimethylformamide (0.03 mL) were added to 5-bromo-2-chlorobenzoic acid (5.0 g, 0.0212 mol) in chloroform (10 mL) and stirred for three hours. The yellow oil obtained by evaporating the solvent under reduced pressure was dissolved in chloroform (10 mL). To this solution, 2,5-difluorophenetole (3.4 g, 0.0214 mol) was added and then aluminum chloride (2.9 g, 0.0214 mol) was added portion wise at −10° C. over five minutes. After the reaction mixture was stirred at 5° C. for two hours, an iced water was added. This was extracted with chloroform three times. After the combined organic layer was washed with 1M hydrochloric acid, water, brine, it was dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain (5-bromo-2-chlorophenyl)(4-ethoxy-2,5-difluorophenyl)methanone (5.59 g, 70%) as a colorless crystal.

Workup

  1. customThe yellow oil obtained
  2. customby evaporating the solvent under reduced pressure
  3. dissolutionwas dissolved in chloroform (10 mL)
  4. stirringAfter the reaction mixture was stirred at 5° C. for two hours
  5. extractionThis was extracted with chloroform three times
  6. washAfter the combined organic layer was washed with 1M hydrochloric acid, water, brine, it
  7. dry with materialwas dried with anhydrous magnesium sulfate
  8. filtrationAfter the desiccant was filtered off
  9. customthe residue obtained
  10. customby evaporating the solvent under reduced pressure
  11. customwas purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-04cec03c3bde420c80e583dbb31dff90
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

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