Water → 4-Chloro-3-fluorobenzoic acid

HRID 2104411Notes

Reaction equation

HRID 2104411 reaction equation
Cl([O-])=O.[Na+].[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[F:14].C([OH:19])(C)(C)C.O>C(OCC)(=O)C>[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]([OH:19])=[O:11])=[CH:8][C:7]=1[F:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 27249854-Chloro-3-FluorobenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 27365364-Chloro-3-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium chlorite (17 g) was added dropwise to a mixture of 4-chloro-3-fluorobenzaldehyde (10 g), amidesulfuric acid (18 g), tert-butyl alcohol (50 mL), and water (50 mL) under ice cooling. The temperature of the mixture was returned gradually to room temperature, and the mixture was stirred for 4 days. The reaction mixture was diluted with ethyl acetate, and the resultant mixture was washed with water, 1N hydrochloric acid, and saturated brine. The organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure. The residue was recrystallized from a solvent mixture of diisopropyl ether and hexane, to thereby give the title compound (11.2 g).

Workup

  1. customwas returned gradually to room temperature
  2. washthe resultant mixture was washed with water, 1N hydrochloric acid, and saturated brine
  3. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue was recrystallized from a solvent mixture of diisopropyl ether and hexane

Sources & evidence

ORD record
ord-dfa7941ec56547aa8c011160d95e3014
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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