Potassium Carbonate → HCID 19831512, compound

HRID 1493488Notes

Reaction equation

HRID 1493488 reaction equation
Br[C:2]1[C:7]([O:8][C:9]([F:14])([F:13])[CH:10]([Cl:12])[F:11])=[CH:6][C:5]([Cl:15])=[CH:4][N:3]=1.[OH:16][C:17]1[CH:30]=[CH:29][C:20]([O:21][CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)C>[Cl:15][C:5]1[CH:6]=[C:7]([O:8][C:9]([F:14])([F:13])[CH:10]([Cl:12])[F:11])[C:2]([O:16][C:17]2[CH:18]=[CH:19][C:20]([O:21][CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:29][CH:30]=2)=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3017597Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl esterHCID 14740064HCID 14740064, compound

Product 1

HCID 19831512HCID 19831512, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

9.75 g (30 mmol) of 2-bromo-5-chloro-3-(2-chloro-1,1,2-trifluoroethoxy)pyridine, 6.94 g (33 mmol) of ethyl 4-hydroxyphenoxypropionate and 6.6 g of anhydrous potassium carbonate in 40 ml of absolute dimethyl sulfoxide were stirred for 9 hours at 80° C. under argon. After cooling, the mixture was diluted with 300 ml of diethyl ether, the potassium carbonate was filtered off, and the organic phase was washed with 5% strength KOH and subsequently with water until neutral. After drying, the compound of Example 1 was obtained in a crude yield of 13.4 g (98% of theory).

Workup

  1. temperatureAfter cooling
  2. filtrationthe potassium carbonate was filtered off
  3. washthe organic phase was washed with 5% strength KOH and subsequently with water until neutral
  4. customAfter drying

Sources & evidence

ORD record
ord-7d2ddbab68754fb38b34151959593541
Source dataset
uspto-grants-1991_06
Patent number
US05021578

Reaction notes

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