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

HRID 448892Notes

Reaction equation

HRID 448892 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-557ab0bb7e8d43a8bb027eee811221a7
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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