Hydrochloric Acid → 5-Bromo-6-(2,4-difluorophenoxy)nicotinic acid

HRID 930933Notes

Reaction equation

HRID 930933 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[OH:20].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CS(C)=O.O>[Br:1][C:2]1[C:3]([O:20][C:14]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=2[F:12])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acid

Product 1

HCID 867210745-Bromo-6-(2,4-difluorophenoxy)nicotinic acidYield 67.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

5-bromo-6-chloronicotinic acid (3 g, 12.69 mmol), 2,4-difluorophenol (3.30 g, 25.4 mmol) and cesium carbonate (16.54 g, 50.8 mmol) were combined in DMSO (25.4 mL), heated at 100° C. for 6 hours, cooled, diluted with 150 mL of iced water and the pH was adjusted to pH 3 with 12M HCl. The resulting solid was collected by filtration, washed with cold water and dried to constant mass to afford the title compound (2.84 g, 64%).

Workup

  1. temperaturecooled
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with cold water
  4. customdried to constant mass

Sources & evidence

ORD record
ord-86af623df793498b870b186bdd4f1d07
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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