Sulfuric Acid → HCID 66995222, compound

HRID 1523548Notes

Reaction equation

HRID 1523548 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.S(=O)(=O)(O)[OH:19].[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:5]([C:8]([NH2:9])=[O:19])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 669950285-Bromo-3-(4-fluorophenoxy)picolinonitrile

Product 1

HCID 66995222HCID 66995222, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask was charged with 5-bromo-3-(4-fluorophenoxy)picolinonitrile (10 g, 34 mmol) and sulfuric acid (50 mL). The reaction was stirred at ambient temperature overnight. Water (500 mL) was added carefully and the mixture was adjusted to pH 5.0 using 50% sodium hydroxide. The mixture was extracted with dichloromethane and ethyl acetate, dried and concentrated to afford 5-bromo-3-(4-fluorophenoxy)picolinamide (10.6 g, 34 mmol, 100% yield) as yellow solid.

Workup

  1. extractionThe mixture was extracted with dichloromethane and ethyl acetate
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6f63c629e7db42f1865eff3b19398dba
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

Loading…