Potassium Carbonate → Acifluorfen-methyl

HRID 444023

Reaction equation

HRID 444023 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].F[C:20]1[CH:21]=[CH:22][C:23]([N+:30]([O-:32])=[O:31])=[C:24]([CH:29]=1)[C:25]([O:27][CH3:28])=[O:26]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[CH:4][C:3]=1[O:12][C:20]1[CH:21]=[CH:22][C:23]([N+:30]([O-:32])=[O:31])=[C:24]([CH:29]=1)[C:25]([O:27][CH3:28])=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27366032-Chloro-4-(trifluoromethyl)phenolHCID 51520495-Fluoro-2-nitrobenzoic acid methyl ester

Product 1

HCID 91642Acifluorfen-methylYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 5-liter, 4-necked flask fitted with a stirrer, thermometer, addition funnel, reflux condenser and drying tube is added dimethyl sulfoxide (200 ml), 2-chloro-4-trifluoromethylphenol) (715 g, 3.64 mole), and anhydrous potassium carbonate (520 g, 3.72 moles). The reaction mixture is stirred at room temperature overnight under a nitrogen atmosphere. Then methyl 5-fluoro-2-nitrobenzoate (724 g, 3.64 moles) is added over a 1 hour period (slight exotherm to 31° C.). After stirring overnight at room temperature, the inorganic solids are removed by filtration and 1700 ml of dimethyl sulfoxide removed under vacuum (1 mm, pot temp. of 85° C., vapor temp. of -40° C.). The residue is diluted with a large volume of carbon tetrachloride and water washed. The organic layer is dried with anhydrous magnesium sulfate and the solvent removed under vacuum to afford 1142 g of methyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (84% yield). Anal. Calcd. for C15H9ClF3NO5 : C, 47.90; H, 2.42; Cl, 9.45; F, 15.20; N, 3.73. Found: C, 47.83; H, 2.47; Cl, 9.15; F, 14.84; N, 3.69.

Workup

  1. customTo a 5-liter, 4-necked flask fitted with a stirrer
  2. additionthermometer, addition funnel
  3. temperaturereflux condenser
  4. customdrying tube
  5. stirringAfter stirring overnight at room temperature
  6. customthe inorganic solids are removed by filtration and 1700 ml of dimethyl sulfoxide
  7. customremoved under vacuum (1 mm, pot temp. of 85° C., vapor temp. of -40° C.)
  8. additionThe residue is diluted with a large volume of carbon tetrachloride and water
  9. washwashed
  10. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  11. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-785e54d179124409b7be29b048edb6cb
Source dataset
uspto-grants-1981_04
Patent number
US04262152

Linked notes

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