Hydrochloric Acid → 5-bromo-4-chloro-2-fluorobenzoic acid

HRID 1485970Notes

Reaction equation

HRID 1485970 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([Cl:11])=[CH:6][C:5]=1[F:12].Cl>C1COCC1.[OH-].[Na+]>[Br:10][C:8]1[C:7]([Cl:11])=[CH:6][C:5]([F:12])=[C:4]([CH:9]=1)[C:3]([OH:13])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 26986196Methyl 5-bromo-4-chloro-2-fluorobenzoate

Product 1

HCID 27732655-bromo-4-chloro-2-fluorobenzoic acidYield 100.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-Bromo-4-chloro-2-fluoro-benzoic acid methyl ester (14.0 g, 52.4 mmol) was stirred vigorously in a mixture of THF (250 ml) and 1N NaOH (200 ml) for 16 hrs. The mixture was acidified to pH 3 with 6N HCl, concentrated partially to remove THF and then extracted with ethyl acetate. The organic phase was washed with water and brine and was dried over Na2SO4. The filtrate was concentrated to yield 5-bromo-4-chloro-2-fluoro-benzoic acid (13.3 g).

Workup

  1. concentrationconcentrated partially
  2. customto remove THF
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialwas dried over Na2SO4
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-312eb60172e14a1994a7dacc91ce96c3
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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