Potassium Carbonate → Haloxyfop-P

HRID 1248088Notes

Reaction equation

HRID 1248088 reaction equation
S([O:5][C@H:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(C)(=O)=O.[Cl:13][C:14]1[C:15]([O:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:13][C:14]1[C:15]([O:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C@H:6]([CH3:12])[C:7]([OH:9])=[O:8])=[CH:27][CH:26]=2)=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:19]=1.[Cl:13][C:14]1[C:15]([O:24][C:25]2[CH:26]=[CH:27][C:28]([O:5][C@H:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:29][CH:30]=2)=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2723759Propanoic acid, 2-[(methylsulfonyl)oxy]-, ethyl ester, (R)-HCID 97959974-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)oxyphenol

Product 2

HCID 448979Haloxyfop-PHCID 54462333HCID 54462333, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid is prepared as follows: A suspension of ethyl (R)-2-mesyloxypropionate (0.392 g, 2.0 mmol), 4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenol (0.578 g, 2.0 mmol) and potassium carbonate (0.276 g, 2.0 mmo.) in 8 ml of DMSO is heated at 80° for 24 hours. The reaction mixture is cooled and worked up to give ethyl (R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionate. The propionate is hydrolyzed by stirring it (0.80 g, 2.22 mmol) in 10 ml of ethanol with sodium hydroxide (0.10 g, 2.50 mmol) in 1 ml of water overnight. The ethanol is then removed in vacuo from the reaction mixture. The residue is acidified with HCl and extracted with ether. The organic fraction is washed with brine until neutral and dried over sodium sulfate. Solvent is removed to give (R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid.

Workup

  1. temperatureis heated at 80° for 24 hours
  2. temperatureThe reaction mixture is cooled

Sources & evidence

ORD record
ord-3c74b34a8b8349dab4d2dc62aede4c5b
Source dataset
uspto-grants-1985_06
Patent number
US04522647

Reaction notes

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