Sulfuric Acid → HCID 66995222, compound

HRID 1511013Notes

Reaction equation

HRID 1511013 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-c5f4052fe7ca426e85f2cc48d13fc7f2
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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