Hydrochloric Acid → 2-Chloro-4-fluoro-5-(3-fluoropyridin-2-yl)benzoic acid

HRID 522135Notes

Reaction equation

HRID 522135 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[OH-].O.Cl>C(O)C>[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 118497072HCID 118497072, compound

Product 1

HCID 1184971782-Chloro-4-fluoro-5-(3-fluoropyridin-2-yl)benzoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 2-chloro-4-fluoro-5-(3-fluoropyridin-2-yl)benzoate (Preparation 36, 240 mg, 0.85 mmol) in ethanol (5 mL) was added 2M LiOH in water (2.1 mL, 4.23 mmol). The reaction was stirred at room temperature for 1 hour before neutralising with 2M HCl (aq). The resulting precipitate was collected, washed with water and dried to afford the title compound as a white solid (160 mg, 70%).

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-55f593576f824427b55ec44877b66e62
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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