1,2-Dichloroethane → 6-chloropyridine-2-sulfonic Acid

HRID 1074222

Reaction equation

HRID 1074222 reaction equation
OC1C=CC(CC(OC)=O)=CC=1.ClCCCl.F[N+:18]1[C:23]([S:24]([O-:27])(=[O:26])=[O:25])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:28]>O>[Cl:28][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([S:24]([OH:27])(=[O:26])=[O:25])[N:18]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 14897827N-Fluoro-6-chloropyridinium-2-sulfonate

Product 1

HCID 27628906-chloropyridine-2-sulfonic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 25 ml egg-plant type flask was flushed with argon, and 83.0 mg (0.5 mmol) of methyl 4-hydroxyphenylacetate, 2 ml of dry 1,2-dichloroethane and 105.7 mg (0.5 mmol) of N-fluoro-2-chloropyridinium-6-sulfonate were charged. The flask was immersed in an oil bath of 80° C. and heated for 22 hours. After completion of the reaction, 20 ml of water was added thereto, and the mixture was extracted three times with 20 ml of methylene chloride. 2-Chloropyridine-6-sulfonic acid formed after the reaction was all transferred to the aqueous layer. The organic layer was washed with water and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by thin layer chromatography (eluent: hexane/diethyl ether=2/1) to obtain 49.4 mg (conversion yield: 63%) of methyl 3-fluoro-4-hydroxyphenylacetate, and 11.2 mg of methyl 4-hydroxyphenylacetate was recovered (recovery rate: 14%).

Workup

  1. additionwere charged
  2. customThe flask was immersed in an oil bath of 80° C.
  3. temperatureheated for 22 hours
  4. additionwas added
  5. extractionthe mixture was extracted three times with 20 ml of methylene chloride

Sources & evidence

ORD record
ord-894124bae0d84af8ad151063e0e4405c
Source dataset
uspto-grants-1990_11
Patent number
US04973697

Linked notes

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