Hydrochloric Acid → 2,6-Difluoro-3-nitrobenzoic acid

HRID 1187294Notes

Reaction equation

HRID 1187294 reaction equation
C([O:8][C:9](=[O:21])[C:10]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[C:11]=1[F:20])C1C=CC=CC=1.[OH-].[Na+].Cl>O1CCCC1.O>[F:20][C:11]1[C:12]([N+:17]([O-:19])=[O:18])=[CH:13][CH:14]=[C:15]([F:16])[C:10]=1[C:9]([OH:21])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 583170052,6-Difluoro-3-nitro-benzoic acid benzyl ester

Product 1

HCID 3026292,6-Difluoro-3-nitrobenzoic acidYield 56.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2,6-difluoro-3-nitro-benzoic acid benzyl ester (47, 750 mg, 2.6 mmol) in 4 mL of tetrahydrofuran and 2 mL of water, sodium hydroxide (0.2 g, 5.0 mmol) is added and the reaction is stirred for 2 hours. The reaction is acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer is concentrated under vacuum to provide the desired compound (48, 300 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer is concentrated under vacuum

Sources & evidence

ORD record
ord-c579b3f9030948b38928ca0b846d3113
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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