Hydrochloric Acid → 1-(3,4-Difluorophenyl)-indole-5-carboxylic acid

HRID 2365592Notes

Reaction equation

HRID 2365592 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([O:20]C)=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59626069Methyl 1-(3,4-difluorophenyl)-indole-5-carboxylate

Product 1

HCID 596260681-(3,4-Difluorophenyl)-indole-5-carboxylic acidYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 1-(3,4-difluorophenyl)-indole-5-carboxylate 1p (3.0 g, 10.4 mmol) and LiOH (1.0 g, 41.8 mmol) in THF (120 mL) and H2O (60 mL) was stirred at room temperature for 5 days. Aqueous 10% HCl solution was added to the reaction mixture to adjust pH=3˜4. The resulting mixture was extracted with EtOAc (2×). The organic solution was washed with aq. NaCl, dried over Na2SO4 and concentrated to give 1q (2.85 g).

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×)
  2. washThe organic solution was washed with aq. NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-364c3f12be2d44c8b1f5aef5e2d4e008
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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