Potassium Carbonate → Methyl 2-(4-(3-fluoro-5-(trifluoromethyl)-2-pyridyloxy)phenoxy}propionate

HRID 728633Notes

Reaction equation

HRID 728633 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].F[C:22]1[C:27]([F:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:24][N:23]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[F:28][C:27]1[C:22]([O:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:13][CH:14]=2)=[N:23][CH:24]=[C:25]([C:29]([F:31])([F:30])[F:32])[CH:26]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl esterHCID 134215472,3-Difluoro-5-(trifluoromethyl)pyridine

Product 1

HCID 177207Methyl 2-(4-(3-fluoro-5-(trifluoromethyl)-2-pyridyloxy)phenoxy}propionate

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A 22 liter (L), 3-necked round-bottom flask with a bottom outlet was fitted with a mechanical stirrer, a condenser topped with a nitrogen inlet, and an addition funnel. Through the funnel, 6.546 kilograms (kg) (33.13 moles) of molten methyl 2-(4-hydroxyphenoxy)propionate, 6.571 kg (47.55 moles) of anhydrous K2CO3 and 319 g (0.99 moles) of tetra-n-butylammonium bromide were added to the reactor. Under constant agitation, the slurry was heated to 66° C. with a steam-water mixture controlled by a microprocessor and 6.026 kg (32.93 moles) of 2,3-difluoro-5-trifluoromethyl-pyridine was added over 15 min. The reaction mixture was heated for 13 hours (hr) at 70°-75° C. after which the product was washed 5 times using a total 37 L of hot water. The washed product was stripped of residual water using a rotary evaporator at 75° C. at a reduced pressure of 30 millimeters (mm) of mercury. A total 10.7 kg of product was collected having a purity of 97.9 percent.

Workup

  1. customtopped with a nitrogen inlet, and an addition funnel
  2. additionwas added over 15 min
  3. temperatureThe reaction mixture was heated for 13 hours (hr) at 70°-75° C. after which the product
  4. washwas washed 5 times
  5. customa rotary evaporator at 75° C. at a reduced pressure of 30 millimeters (mm) of mercury
  6. customA total 10.7 kg of product was collected

Sources & evidence

ORD record
ord-b2625484a9144f0c9685168f873d3a6d
Source dataset
uspto-grants-1991_09
Patent number
US05049675

Reaction notes

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