Hydrochloric Acid → 4-Ethyldibenzothiophene

HRID 1293453Notes

Reaction equation

HRID 1293453 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH:6]1[C:14]2[C:13]3C=C[CH:17]=[CH:18][C:12]=3[S:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.C(I)C.Cl>C1COCC1>[CH2:3]([C:2]1[C:1]2[S:11][C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:14]=3[C:13]=2[CH:12]=[CH:18][CH:17]=1)[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3023DibenzothiopheneHCID 6340IodoethaneHCID 178418339Butyllithium

Product 1

HCID 1849884-Ethyldibenzothiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (108 mmols, 46 ml of 2.4M solution in hexane) was added to a stirred solution of dibenzothiophene (10 g, 54 mmole) in dried THF (150 ml) at 0° C. over a period of 1 hr under dry N2 atmosphere. This reaction mixture was stirred 5 hrs at room temperature then the reaction mixture was cooled to −70° C. and a solution of ethyl iodide in dry THF was added dropwise and stirred at room temperature for over night. This reaction mixture was poured slowly into a cold 1N HCl (200 ml). Organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×500 ml). Organic layers mixed together and concentrated to dryness to get crude product. The crude product was purified by silica gel column chromatography.

Workup

  1. temperaturethe reaction mixture was cooled to −70° C.
  2. stirringstirred at room temperature for over night
  3. customOrganic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×500 ml)
  5. additionOrganic layers mixed together
  6. concentrationconcentrated to dryness
  7. customto get crude product
  8. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e75aa5c273984077958939069ed96a8f
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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