1-Bromo-3-methylbutane → 1-Bromo-4-isopentylthiobenzene

HRID 1590430Notes

Reaction equation

HRID 1590430 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15]>CC(C)=O>[CH3:15][CH:14]([CH3:16])[CH2:13][CH2:12][S:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutane2×HCID 14798Sodium HydroxideHCID 660494-Bromothiophenol2×

Product 1

HCID 125212431-Bromo-4-isopentylthiobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 15 g (79 mmol) of 4-bromo-thiophenol (Compound 42), 3.16 g (79 mmol) of powdered sodium hydroxide and 150 ml of acetone was heated at reflux for 15 minutes. The refluxing mixture was then treated dropwise with a solution of 12 g (79 mmol) of 1-bromo-3-methylbutane (Compound 51) in 25 ml of acetone and then refluxed for a further 18 hours. The mixture was allowed to cool and the solvent removed in-vacuo. The residue was taken up in 25 ml of water and the mixture basified with 2 N NaOH solution. The mixture was extracted with ether and the combined ether extracts washed successively with 1 N NaOH, water and saturated NaCl and then dried (MgSO4). The solvent was removed in-vacuo and the residue distilled (113-117 degrees C., 0.2 mm) to give the title compound as a colourless oil. PMR (CDCl3): & 0.93 (6H, d, J~6.6 Hz), 1.47-1.58 (2H, m), 1.65-1.80 (1H, m), 2.90 (2H, t, J~7.8 Hz), 7.18 (2H, d, J~8.6 Hz), 7.39 (2H, d, J~8 6 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 minutes
  3. temperaturerefluxed for a further 18 hours
  4. temperatureto cool
  5. customthe solvent removed in-vacuo
  6. extractionThe mixture was extracted with ether
  7. washthe combined ether extracts washed successively with 1 N NaOH, water and saturated NaCl
  8. dry with materialdried (MgSO4)
  9. customThe solvent was removed in-vacuo
  10. distillationthe residue distilled (113-117 degrees C., 0.2 mm)

Sources & evidence

ORD record
ord-00b7fcd4f5c744228d996106f17ed8a9
Source dataset
uspto-grants-1993_04
Patent number
US05202471

Reaction notes

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