Sodium Hydroxide → 2,4-Dichloro-5-(3-fluoropyridin-2-yl)benzoic acid

HRID 522137Notes

Reaction equation

HRID 522137 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl: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].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:11]=[C:10]([Cl: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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118497135Methyl 2,4-dichloro-5-(3-fluoropyridin-2-yl)benzoate

Product 1

HCID 1184971172,4-Dichloro-5-(3-fluoropyridin-2-yl)benzoic acidYield 32.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the organic solution of methyl 2,4-dichloro-5-(3-fluoropyridin-2-yl)benzoate (from Preparation 43A, 1.95 mol) was added a solution of sodium hydroxide (234 g, 5.85 mol) in water (2.8 L) and the reaction stirred at room temperature for 1 hour. The mixture was concentrated in vacuo to remove organic solvents to a volume of approximately 5 L. The remaining aqueous phase was washed with ethyl acetate (3×2 L) and then acidified to pH2 with aqueous HCl (2 M). The resulting precipitate was collected by filtration and washed with water (2 L). The solid was ground to a fine powder and slurried with diethyl ether (2.5 L) and filtered to afford the title compound as an off-white solid (181 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove organic solvents to a volume of approximately 5 L
  3. washThe remaining aqueous phase was washed with ethyl acetate (3×2 L)
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water (2 L)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-bb140576e4e14b1e9a37172373eaaf17
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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