1,6-Dibromohexane → 6-Bromohexylbut-3-enyl ether

HRID 2118335Notes

Reaction equation

HRID 2118335 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8].[CH2:9]([OH:13])[CH2:10][CH:11]=[CH2:12].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:13][CH2:9][CH2:10][CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 693893-Buten-1-ol

Product 1

HCID 858619736-Bromohexylbut-3-enyl ether

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

A mixture of 1,6-dibromohexane (18.30 g), 3-butene-1-ol (2.15 ml), and tetrabutylammonium bromide (0.81 g) were stirred vigorously with 10N NaOH (25 ml) at room temperature under nitrogen for 18 h. The reaction mixture was partitioned between water and EtOAc. The organic phase was washed with brine, dried (MgSO4), and evaporated to dryness. The residual oil was purified on a silica SPE bond elut cartridge (100 g). The excess 1,6-dibromohexane was eluted with cyclohexane. Elution with 5% diethyl ether in cyclohexane and removal of the solvent under reduced pressure gave the title compound (4.52 g). Tlc-silica (5% diethyl ether in cyclohexane) Rf=0.44.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customThe residual oil was purified on a silica SPE bond elut cartridge (100 g)
  6. washThe excess 1,6-dibromohexane was eluted with cyclohexane
  7. washElution
  8. customwith 5% diethyl ether in cyclohexane and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-fc355d73053749a08226f8737310dfeb
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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