Acetic Acid → HCID 20513440, compound

HRID 1164120Notes

Reaction equation

HRID 1164120 reaction equation
C[O:2][C:3]1[C:8]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:17]([CH3:20])[C:18]#N.C(O)(=[O:23])C>I>[CH3:18][CH:17]1[C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([S:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[C:3]=2[O:2][C:20]1=[O:23]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 20513496HCID 20513496, compound

Product 1

HCID 20513440HCID 20513440, compound

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Procedure

A solution of 2-[2-methoxy-3-(2-fluorophenylthio)phenyl]propionitrile (3.2 g) in hydriodic acid (58%, 20 ml) and acetic acid (40 ml) was refluxed under heating for 20 hours, and acetic acid was distilled off under reduced pressure. To the residue were added water and aqueous sodium bicarbonate, and the mixture was extracted with diethyl ether. The extract was washed with dil. aqueous sodium hydrogen sulfite and water in turn, dried and evaporated under reduced pressure. The oily residue (2 g) was purified by column chromatography (silica gel 40 g, toluene) to give oily 3-methyl-7-(2-fluorophenylthio)-2,3-dihydrobenzofuran-2-one (1.3 g).

Workup

  1. temperatureunder heating for 20 hours
  2. distillationacetic acid was distilled off under reduced pressure
  3. additionTo the residue were added water and aqueous sodium bicarbonate
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe extract was washed with dil. aqueous sodium hydrogen sulfite and water in turn
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe oily residue (2 g) was purified by column chromatography (silica gel 40 g, toluene)

Sources & evidence

ORD record
ord-11a3c47dbd7a4f31b21d341ff8ed65df
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

Loading…