Hydrochloric Acid → 5'-(1-Methylethyl)-5-phenyl[2,2'-bithienyl]

HRID 2165129Notes

Reaction equation

HRID 2165129 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([C:11]2[S:15][C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)=[CH:13][CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl[CH:22]([CH3:24])[CH3:23].Cl>C(Cl)Cl>[CH3:23][CH:22]([C:18]1[S:17][C:16]([C:14]2[S:15][C:11]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:12][CH:13]=2)=[CH:20][CH:19]=1)[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 63612-ChloropropaneHCID 4547572,2'-Bithiophene, 5-phenyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 148236285'-(1-Methylethyl)-5-phenyl[2,2'-bithienyl]Yield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred suspension of 0.55 gram (0.0041 mole) of aluminum chloride in 40 ml of methylene chloride was cooled to 0° C., and a solution of 1.0 gram (0.0041 mole) of 5-phenyl[2,2'-bithienyl], 0.9 gram (0.005 mole) of 2-chloropropane in 40 ml of methylene chloride was added dropwise. Upon completion of addition the reaction mixture stirred at 0° C. for 30 minutes, then was allowed to warm to ambient temperature where it stirred for 16 hours. The reaction mixture was poured into a mixture of ice and aqueous 10% hydrochloric acid. The layers were separated and the aqueous phase was extracted with three 25 ml portions of diethyl ether. The organic layers were combined and the combination washed in succession with a solution of aqueous 5% sodium bicarbonate, water, and an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished with 100% hexane. The appropriate fractions were combined and concentrated under reduced pressure to yield 0.7 gram of 5'-(1-methylethyl)-5-phenyl[2,2'-bithienyl]; m.p. 104°-106° C.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperatureto warm to ambient temperature where it
  3. stirringstirred for 16 hours
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with three 25 ml portions of diethyl ether
  6. washthe combination washed in succession with a solution of aqueous 5% sodium bicarbonate, water
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure to a residue
  10. washElution
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43ba800ac75d49cc85b8a2362d2e1437
Source dataset
uspto-grants-1990_07
Patent number
US04939165

Reaction notes

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