Lithium hydroxide, monohydrate → 2-[3-(Ethylsulfanyl)phenoxy]-5-fluoronicotinic acid

HRID 724285Notes

Reaction equation

HRID 724285 reaction equation
O.[OH-].[Li+].[CH2:4]([S:6][C:7]1[CH:8]=[C:9]([CH:23]=[CH:24][CH:25]=1)[O:10][C:11]1[N:21]=[CH:20][C:19]([F:22])=[CH:18][C:12]=1[C:13]([O:15]CC)=[O:14])[CH3:5]>O1CCCC1.O>[CH2:4]([S:6][C:7]1[CH:8]=[C:9]([CH:23]=[CH:24][CH:25]=1)[O:10][C:11]1[N:21]=[CH:20][C:19]([F:22])=[CH:18][C:12]=1[C:13]([OH:15])=[O:14])[CH3:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21877167HCID 21877167, compound

Product 1

HCID 218771352-[3-(Ethylsulfanyl)phenoxy]-5-fluoronicotinic acidYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate (1.37 g, 33 mmol) was added to a solution of ethyl 2-[3-(ethylsulfanyl)phenoxy]-5-fluoronicotinate (4.21 g, 13 mmol) in tetrahydrofuran (50 ml) and water (30 ml). The mixture was stirred for 4 h, then the volatile solvent was removed under reduced pressure and the residue partitioned between diethyl ether and 2N hydrochloric acid. The organic phase was washed with water, dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by flash column chromatography using dichloromethane:methanol:acetic acid (95:5:0.5) as eluant to give 2-[3-(ethylsulfanyl)phenoxy]-5-fluoronicotinic acid (3.45 g) as a white solid.

Workup

  1. customthe volatile solvent was removed under reduced pressure
  2. customthe residue partitioned between diethyl ether and 2N hydrochloric acid
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-ef72b7155f894f42b96cdd4734cf978d
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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