1,3-Dibromopropane → 1,1-bis(phenylsulfonyl)cyclobutane

HRID 2212061Notes

Reaction equation

HRID 2212061 reaction equation
[C:1]1([S:7]([CH2:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23]Br.[OH-].[Na+].[Cl-].[NH4+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:1]1([S:7]([C:10]2([S:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)(=[O:13])=[O:12])[CH2:23][CH2:22][CH2:21]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 76948(Methylenebis(sulphonyl))bisbenzene

Product 1

HCID 118098431,1-bis(phenylsulfonyl)cyclobutane

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of bis(phenylsulfonyl)methane (30 g, 100 mmol), tetra-n-butylammonium bromide (3 g, 9.3 mmol), 1,3-dibromopropane (30 ml), dichloromethane (600 ml) and 50% aqueous sodium hydroxide (150 ml) was stirred at room temperature for 3 days. The mixture was poured onto saturated aqueous ammonium chloride solution and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was crystallised from i-hexane:diethyl ether to give the title product as a white solid. Yield−24 g (71%).

Workup

  1. extractionextracted into dichloromethane
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was crystallised from i-hexane

Sources & evidence

ORD record
ord-a833b0e05c444e18887d18f7b58e53a2
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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