1,4-Dibromobutane → 4-(4-Bromobutyl)-1-(1,3-dithian-2-yl)ethylbenzene

HRID 1780132Notes

Reaction equation

HRID 1780132 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[S:15][CH2:14][CH2:13][CH2:12][S:11]2)[CH3:9])=[CH:4][CH:3]=1.C([Li])(CC)C.[Br:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.C(OCC)(=O)C>O1CCCC1>[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:10]2[S:15][CH2:14][CH2:13][CH2:12][S:11]2)[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 80561,4-DibromobutaneHCID 8857Ethyl AcetateHCID 219601124-Bromo-1-(1,3-dithian-2-yl)ethylbenzeneHCID 178418400CID 53628100

Product 1

HCID 219601294-(4-Bromobutyl)-1-(1,3-dithian-2-yl)ethylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-1-(1,3-dithian-2-yl)ethylbenzene (27.2 g, 94 mmol) in tetrahydrofuran (200 ml) was charged with sec-butyllithium (99 ml, 1.3M in cyclohexane, 0.13 mole) dropwise at -78° C. under nitrogen. The mixture was stirred at ambient temperature for 1.5 hours, and then quenched with 1,4-dibromobutane (42 g, 0.2 mole). After being stirred for 3 hours, the mixture was poured into ethyl acetate, and then washed with water and brine. The organic solution was then dried (Na2SO4) and concentrated to an oil. The crude product was purified by flash chromatography over a silica gel column. The 4-(4-bromobutyl)-1-(1,3-dithian-2-yl)-ethylbenzene thus purified was a light oil, 22.3 g.

Workup

  1. stirringAfter being stirred for 3 hours
  2. washwashed with water and brine
  3. dry with materialThe organic solution was then dried (Na2SO4)
  4. concentrationconcentrated to an oil
  5. customThe crude product was purified by flash chromatography over a silica gel column
  6. customThe 4-(4-bromobutyl)-1-(1,3-dithian-2-yl)-ethylbenzene thus purified

Sources & evidence

ORD record
ord-73c85551554b4f3ba38f591e3536ebab
Source dataset
uspto-grants-1997_05
Patent number
US05629326

Reaction notes

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