Potassium Carbonate → 5-[2-Chloro-6-fluoro-4-(trifluoromethyl)phenoxy]-2,3-dihydro-2-oxobenzoxazole-3-acetic acid methyl ester

HRID 414152Notes

Reaction equation

HRID 414152 reaction equation
[C:1]([CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([OH:15])[CH:13]=[CH:14][C:9]=2[O:8][C:7]1=[O:16])([O:3][CH3:4])=[O:2].[Cl:17][C:18]1[CH:19]=[C:20]([C:26]([F:29])([F:28])[F:27])[CH:21]=[C:22]([F:25])[C:23]=1F.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:1]([CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([O:15][C:23]3[C:22]([F:25])=[CH:21][C:20]([C:26]([F:27])([F:29])[F:28])=[CH:19][C:18]=3[Cl:17])[CH:13]=[CH:14][C:9]=2[O:8][C:7]1=[O:16])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2736496Benzene, 1-chloro-2,3-difluoro-5-(trifluoromethyl)-HCID 143692263-Carbomethoxymethyl-5-hydroxybenzoxazolone

Product 1

HCID 143692275-[2-Chloro-6-fluoro-4-(trifluoromethyl)phenoxy]-2,3-dihydro-2-oxobenzoxazole-3-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 1.37 grams (0.006 mole) of 3-carbomethoxymethyl-5-hydroxybenzoxazolone, 1.52 grams (0.007 mole) of 3-chloro-4,5-difluorobenzotrifluoride, 1.26 grams (0.009 mole) of potassium carbonate and 25 milliliters of dimethylsulfoxide was stirred in a water bath maintained at 75° C. until HPLC analysis indicated substantially complete consumption of starting material. The mixture was then poured into 100 milliliters of water, cooled in an ice bath and extracted twice with methylene chloride. The organic extracts were further extracted with three portions of water, dried over anhydrous magnesium sulfate and evaporated at reduced pressure. The oily residue was taken up in hexane, solidified, filtered and recrystallized from methanol affording 0.67 gram of material confirmed by NMR analysis as the desired product.

Workup

  1. customconsumption of starting material
  2. additionThe mixture was then poured into 100 milliliters of water
  3. temperaturecooled in an ice bath
  4. extractionextracted twice with methylene chloride
  5. extractionThe organic extracts were further extracted with three portions of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated at reduced pressure
  8. filtrationfiltered
  9. customrecrystallized from methanol affording 0.67 gram of material

Sources & evidence

ORD record
ord-4e88c220d880462fa3abff92ae2d2372
Source dataset
uspto-grants-1988_12
Patent number
US04790868

Reaction notes

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