Hydrochloric Acid → 5-(3-Bromophenoxy)-3-(3-methoxyphenylthio)picolinic acid

HRID 335234Notes

Reaction equation

HRID 335234 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][C:6]1[CH:7]=[C:8]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[C:9]([C:12]#N)=[N:10][CH:11]=1.[OH-:26].[K+].CCO.Cl.[OH2:32]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][C:6]1[CH:7]=[C:8]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[C:9]([C:12]([OH:32])=[O:26])=[N:10][CH:11]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 669955395-(3-Bromophenoxy)-3-(3-methoxyphenylthio)picolinonitrile

Product 1

HCID 669944425-(3-Bromophenoxy)-3-(3-methoxyphenylthio)picolinic acidYield 100%

Procedure

A 25 mL round-bottomed flask was charged with 5-(3-bromophenoxy)-3-(3-methoxyphenylthio)picolinonitrile (225 mg, 0.544 mmol), potassium hydroxide (2.5 M, 1.09 mL, 2.72 mmol), and EtOH (5 mL). The reaction was heated to reflux overnight. After cooling to room temperature the reaction was poured into water and pH adjusted with 1N HCl to ˜pH=3. The cloudy solution was extracted with CH2Cl2. The organic layer was dried over sodium sulfate, filtered and concentrated to afford the title compound (235 mg, 100%) which was taken forward without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. extractionThe cloudy solution was extracted with CH2Cl2
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-803d5b9e320b42098ca8755c71251aaf
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

Loading…