Chlorobenzene → 5-Chloro-3-methyl-2-phenyl-1-benzothiophene

HRID 2164137Notes

Reaction equation

HRID 2164137 reaction equation
ClC1C=CC(C[CH:9]([C:17]([CH:19]([CH2:27][C:28]2[CH:33]=[CH:32][C:31](Cl)=[CH:30]C=2)[S:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=O)SC2C=CC=CC=2)=CC=1.[Cl:35]C1C=CC=CC=1>>[Cl:35][C:24]1[CH:23]=[CH:22][C:21]2[S:20][C:19]([C:27]3[CH:28]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:17]([CH3:9])[C:26]=2[CH:25]=1

Participants

3

Reactant 2

HCID 7964ChlorobenzeneHCID 131711410p-Chlorophenylthiophenylmethylmethyl ketone

Product 1

HCID 8219825-Chloro-3-methyl-2-phenyl-1-benzothiophene

Conditions

Temperature
180 °C

Procedure

55.7 parts by weight of p-chlorophenylthiophenylmethylmethyl ketone and 500 parts by weight polyphosphoric acid are combined in a stoppered flask and heated with stirring for 3.5 hours at 180° C. 350 Parts by volume of chlorobenzene is added to the reaction mixture and the resulting solution is heated at reflux temperature for an additional hour. After cooling the organic phase of this reaction solution is decanted off; the inorganic phase is dissolved in ice water and extracted once each with benzene and ethyl ether. The combined organic phases are then washed once with a saturated solution of sodium bicarbonate, washed once with brine, and dried over magnesium sulfate. Concentration of this solution in vacuo affords a dark solid. Crystallization of this solid (2xs) from heptane affords a brown solid. Sublimation at 135° C/0.1mm of this brown solid affords 5-chloro-3-methyl-2-phenylbenzo[b]thiophene, melting at 108.5°-110° C. This compound is represented by the following structural formula. ##STR10##

Workup

  1. temperatureheated
  2. temperaturethe resulting solution is heated
  3. temperatureat reflux temperature for an additional hour
  4. temperatureAfter cooling the organic phase of this reaction solution
  5. customis decanted off
  6. dissolutionthe inorganic phase is dissolved in ice water
  7. extractionextracted once each with benzene and ethyl ether
  8. washThe combined organic phases are then washed once with a saturated solution of sodium bicarbonate
  9. washwashed once with brine
  10. dry with materialdried over magnesium sulfate
  11. customConcentration of this solution in vacuo affords a dark solid
  12. customCrystallization of this solid (2xs) from heptane
  13. customaffords a brown solid

Sources & evidence

ORD record
ord-df083cc5f7484a98a2c3a1fad5bd9e7c
Source dataset
uspto-grants-1979_01
Patent number
US04137414

Reaction notes

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