Sulfamic Acid → 4-Chloro-3-fluorobenzoic acid

HRID 902884Notes

Reaction equation

HRID 902884 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].S(N)(=O)(=O)[OH:16].C(O)(C)(C)C>C(OCC)(=O)C.O>[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]([OH:16])=[O:11])=[CH:8][C:7]=1[F:14]

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 6386tert-ButanolHCID 27249854-Chloro-3-FluorobenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 27365364-Chloro-3-fluorobenzoic acidYield 101.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium chlorite (17 g) was added portionwise to a mixture solution composed of 4-chloro-3-fluorobenzaldehyde (10 g), amidosulfuric acid (18 g), tert-butyl alcohol (50 ml) and water (50 ml) under ice cooling, and the mixture was stirred for 4 days while the temperature of the system was gradually raised to room temperature. The reaction mixture was diluted with ethyl acetate and washed with water, 1N hydrochloric acid and saturated aqueous solution of sodium chloride. After the resultant organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, the resultant residue was recrystallized from a mixed solvent of diisopropyl ether and hexane to obtain the title compound (11.2 g).

Workup

  1. washwashed with water, 1N hydrochloric acid and saturated aqueous solution of sodium chloride
  2. dry with materialAfter the resultant organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe resultant residue was recrystallized from a mixed solvent of diisopropyl ether and hexane

Sources & evidence

ORD record
ord-dbbf2f129ea84d02988b5f8cd3b5f10e
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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