1-Bromo-2,2-dimethylpropane → 1-Methyl-4-(neopentylsulfonyl)benzene

HRID 911453Notes

Reaction equation

HRID 911453 reaction equation
[Na+].[C:2]1([CH3:11])[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12](Br)[C:13]([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C.O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:12][C:13]([CH3:16])([CH3:15])[CH2:14][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:11])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

6

Reactant 2

HCID 124151-Bromo-2,2-dimethylpropaneHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 41535251-Methyl-4-(neopentylsulfonyl)benzeneYield 45.4%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

In a sealed tube, dissolve p-toluenesulfinic acid sodium salt (5.71 g, 32.1 mmol) in DMF (20 mL) and water (10 mL). Add neo-pentyl bromide (6.3 mL, 48 mmol) and tetrabutylammonium iodide (592 mg, 1.60 mmol) and heat the mixture at 145° C. overnight. Cool the reaction to ambient temperature, dilute with water and extract 3 times with EtOAc. Dry over anhydrous Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to give the desired intermediate as a colorless oil (3.3 g, 45%).

Workup

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. extractionextract 3 times with EtOAc
  4. dry with materialDry over anhydrous Na2SO4
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-ce32e21fdebf42658270f1bf1322a2e7
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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