Hydrochloric Acid → 5-Bromo-2-(6-fluoropyridin-2-yloxy)benzoic acid

HRID 335825Notes

Reaction equation

HRID 335825 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:16]=[C:12]([C:13]([OH:15])=[O:14])[C:11]([OH:17])=[CH:10][CH:9]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](F)[N:20]=1.Cl>CS(C)=O.O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([F:18])[N:20]=2)=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69725-Bromosalicylic acidHCID 10796Cesium carbonateHCID 739342,6-Difluoropyridine

Product 1

HCID 673831645-Bromo-2-(6-fluoropyridin-2-yloxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of cesium carbonate (3.20 mL, 40.0 mmol), 5-bromosalicylic acid (4.34 g, 20.00 mmol) and 2,6-difluoropyridine (5.52 g, 48.0 mmol) in 8 mL of DMSO was stirred at 110° C. for 3 h. After cooling to rt, the reaction mixture was dissolved in water and the pH was adjusted to ˜3 with 1 N HCl. The reaction mixture was extracted with EtOAC (3×25 mL), washed with brine and evaporated to dryness to give crude 5-bromo-2-(6-fluoropyridin-2-yloxy)benzoic acid which was used directly in the next step.

Workup

  1. temperatureAfter cooling to rt
  2. extractionThe reaction mixture was extracted with EtOAC (3×25 mL)
  3. washwashed with brine
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-2f9290cd7e8e42b58c12060726a14682
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…