Potassium Carbonate → HCID 67119435, compound

HRID 384831Notes

Reaction equation

HRID 384831 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:14]1[C:15]([CH3:29])=[CH:16][C:17]([N+:26]([O-:28])=[O:27])=[C:18]([CH:25]=1)[C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[CH3:29][C:15]1[C:14]([O:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=2)=[CH:25][C:18]([C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])=[C:17]([N+:26]([O-:28])=[O:27])[CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 67119436HCID 67119436, compound

Product 1

HCID 67119435HCID 67119435, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
102.5 °C

Procedure

Dimethylacetamide (716 ml), 170 g of 4-trifluoromethoxyphenol, 246 g of isopropyl 5-chloro-4-methyl-2-nitrobenzoate, and 263.9 g of potassium carbonate were added into a 2000-ml glass flask equipped with a stirring device, a thermometer, and a reflux condenser under a nitrogen atmosphere, and the temperature of the contents of the flask was raised to 100 to 105° C. with stirring. A reaction was allowed to proceed at the same temperature for 37 hr, and 360 ml of dimethylacetamide was then removed by evaporation under the reduced pressure. The reaction solution was poured into 2 L of ice-water, and 1.7 L of ethyl acetate was added thereto. The mixture was stirred and was allowed to stand, followed by separation. The ethyl acetate layer was washed with a 1.5% aqueous sodium hydroxide solution and brine and was concentrated under the reduced pressure to give isopropyl 4-methyl-2-nitro-5-(4-(trifluoromethoxy)phenoxy)benzoate (373.3 g, yield: 97.9%).

Workup

  1. customequipped with a stirring device
  2. custom360 ml of dimethylacetamide was then removed by evaporation under the reduced pressure
  3. additionThe reaction solution was poured into 2 L of ice-water, and 1.7 L of ethyl acetate
  4. additionwas added
  5. stirringThe mixture was stirred
  6. customfollowed by separation
  7. washThe ethyl acetate layer was washed with a 1.5% aqueous sodium hydroxide solution and brine
  8. concentrationwas concentrated under the reduced pressure

Sources & evidence

ORD record
ord-d1ad06b617d24c8696e757e9324be3ad
Source dataset
uspto-grants-2013_02
Patent number
US08367833B2

Reaction notes

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