Hydrochloric Acid → 3-(2-Chloropyridin-4-yloxy)-4-fluorobenzoic acid

HRID 521772Notes

Reaction equation

HRID 521772 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([O:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([Cl:18])[CH:13]=2)[CH:5]=1.[OH-].[Li+].O.Cl>O1CCCC1>[Cl:18][C:14]1[CH:13]=[C:12]([O:11][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=2[F:10])[C:3]([OH:19])=[O:2])[CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 581679163-(2-Chloropyridin-4-yloxy)-4-fluorobenzoic acid methyl ester

Product 1

HCID 581677923-(2-Chloropyridin-4-yloxy)-4-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Chloropyridin-4-yloxy)-4-fluorobenzoic acid methyl ester (2.81 g, 10.0 mmol) was dissolved in tetrahydrofuran (15 mL) and mixed with 2M lithium hydroxide (15 mL, 30 mmol). The suspension was stirred for 5 h. To the reaction was added water, then extracted with EtOAc. The aqueous layer was treated with 6M HCl (5 mL, 30 mmol) and then extracted with EtOAc (3×25 mL). The extract was dried (MgSO4), filtered and evaporated to 3-(2-Chloropyridin-4-yloxy)-4-fluorobenzoic acid. Yield: 2.22 g, 83%.

Workup

  1. extractionextracted with EtOAc
  2. extractionextracted with EtOAc (3×25 mL)
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to 3-(2-Chloropyridin-4-yloxy)-4-fluorobenzoic acid

Sources & evidence

ORD record
ord-c4b15a3042704b44b5fe25252a632217
Source dataset
uspto-grants-2016_05
Patent number
US09328103B2

Reaction notes

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