Tetrahydrofuran → 4-Chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid

HRID 1848605Notes

Reaction equation

HRID 1848605 reaction equation
C1COCC1.C[O:7][C:8](=[O:24])[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][N:17]=2)[CH:10]=1.O[Li].O>O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]([OH:24])=[O:7])=[CH:10][C:11]=1[C:16]1[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 686021224-Chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid methyl ester

Product 1

HCID 686040024-Chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acidYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of THF (15 mL) and water (1 mL) containing 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid methyl ester (1.7 g, 5.4 mmol) and LiOH.H2O (0.68 g, 16.1 mmol) was stirred at room temperature for 12 hrs. The mixture was acidified and extracted with ethyl acetate. The organic layer was washed with brine and water and was dried. Filtration and concentration gave 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid as a white solid (1.4 g). MS (M+H)+: 301.6, tR=7.048 min (method 2)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine and water
  3. customwas dried
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-18377b5457d14494abbab171cde88ba6
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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