1-Bromo-3-methylbutane → Butane, 1,1'-thiobis[3-methyl-

HRID 865821Notes

Reaction equation

HRID 865821 reaction equation
[CH2:1](Br)[CH2:2][CH:3]([CH3:5])[CH3:4].O.O.O.O.O.O.O.O.O.[S-2:16].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([S:16][CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 78911-Bromo-3-methylbutaneHCID 73972Sodium sulfide nonahydrate

Product 1

HCID 10990Butane, 1,1'-thiobis[3-methyl-Yield 91%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Isoamyl bromide (21.88 g, 0.21 mol) and tetrabutylammonium bromide (1.61 g, 5 mmol) were added to a solution of sodium sulfide nonahydrate (24.02 g, 0.10 mol) in water (50 ml) and the mixture was refluxed with stirring for 6 h. The organic layer was separated, the aqueous layer was extracted with pentane (25 ml). The extract was combined with the organic layer and dried with anhydrous magnesium sulfate. Distillation gave 15.85 g, 91% of a colorless liquid, bp 49°-50° C./0.1 mm Hg, n20D=1.4514, >99% GC pure; 1H NMR (CDCl3) δ 0.95 (d, J=6 Hz, 12H, CH3), 1.47 (q, J=6 Hz, 4H, CH2), 1.68 (septet, J=6 Hz, 2H, CH), 2.51 (t, J=6 Hz, 4H, CH2).

Workup

  1. temperaturethe mixture was refluxed
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with pentane (25 ml)
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationDistillation

Sources & evidence

ORD record
ord-377ab4451b114e5bb144c178981b522e
Source dataset
uspto-grants-1996_10
Patent number
US05567849

Reaction notes

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