1,3-Dibromopropane → HCID 21963798, compound

HRID 2212065Notes

Reaction equation

HRID 2212065 reaction equation
[Li].C1(S([C:11]2([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:14][CH2:13][CH2:12]2)(=O)=O)C=CC=CC=1.[Br:24][CH2:25][CH2:26][CH2:27]Br>O1CCCC1>[Br:24][CH2:25][CH2:26][CH2:27][C:11]1([S:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)(=[O:16])=[O:17])[CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 3028194LithiumHCID 118098431,1-bis(phenylsulfonyl)cyclobutane

Product 1

HCID 21963798HCID 21963798, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium napthtalenide in tetrahydrofuran (4.3M, 60 ml) was added to a stirred solution of 1,1-bis(phenylsulfonyl)cyclobutane (4.15 g, 12.35 mmol) at −78° C. over 20 min. The mixture was stirred for 15 min. and 1,3-dibromopropane (10 ml) was added in one portion. The cold bath was removed and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was treated with saturated aqueous ammonium chloride solution and extracted into ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified on silica gel to give the title product (2.55 g, 65%).

Workup

  1. customThe cold bath was removed
  2. stirringthe mixture was stirred at ambient temperature for 2 hours
  3. additionThe reaction mixture was treated with saturated aqueous ammonium chloride solution
  4. extractionextracted into ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-41ce711b69f0474ca476e181a4a36a3d
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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