1,2-Dichloroethane → [6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophen-3-yl](phenyl)methanone

HRID 2163316Notes

Reaction equation

HRID 2163316 reaction equation
ClCCCl.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=3[CH:17]=2)=[CH:9][CH:8]=1.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=3[C:17]=2[C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7412Benzoyl chlorideHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22753379[6-Methoxy-2-(4-methoxyphenyl)-1-benzothiophen-3-yl](phenyl)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 300 ml. of 1,2-dichloroethane maintained at 0° C. were added 6.0 g. (0.022 mole) of 2-(4-methoxyphenyl)-6-methoxybenzothiophene and 3.10 g. (0.022 mole) of benzoyl chloride. The mixture was stirred vigorously, and 3.2 g. (0.024 mole) of aluminum chloride were added in small portions. The resulting red solution was stirred for one hour, and water then was added. The yellow organic layer was separated, washed with 200 ml. of 1N sodium hydroxide and then with 200 ml. of saturated sodium chloride solution. The mixture then was dried over potassium carbonate, and the solvent was evaporated to give a pale yellow solid which was purified by chromatography over silica gel using benzene and 5% ethyl acetate in benzene as eluant. The appropriate fractions gave product as yellow crystals. The product was recrystallized from methanol to obtain 3.5 g. (42 percent) of 2-(4-methoxyphenyl)-3-benozyl-6-methoxybenzothiophene, melting point 110.5°-111° C.

Workup

  1. additionwere added 6.0 g
  2. stirringThe resulting red solution was stirred for one hour
  3. customThe yellow organic layer was separated
  4. washwashed with 200 ml
  5. dry with materialThe mixture then was dried over potassium carbonate
  6. customthe solvent was evaporated
  7. customto give a pale yellow solid which
  8. customwas purified by chromatography over silica gel
  9. customThe appropriate fractions gave product as yellow crystals
  10. customThe product was recrystallized from methanol
  11. customto obtain 3.5 g

Sources & evidence

ORD record
ord-195e3913920d4ab8ad8e73af3017a1a7
Source dataset
uspto-grants-1979_01
Patent number
US04133814

Reaction notes

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