1-Butanol → 6-Bromohexyl 4-(3-bromophenyl)butyl ether

HRID 2118318Notes

Reaction equation

HRID 2118318 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:13][C:12]1[CH:7]=[C:8]([CH2:4][CH2:3][CH2:2][CH2:1][O:5][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Br:13])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 2631-ButanolHCID 123681,6-DibromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 218954686-Bromohexyl 4-(3-bromophenyl)butyl ether

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A stirred mixture of 4-3-bromophenyl) butan-1-ol (18 g) (EP 0 995 752A1), 1,6 dibromohexane (48 ml), tetrabutylammonium bromide (1.5 g) and 50% aqueous sodium hydroxide solution (500 ml) was stirred for 2 days at ambient temperature. The mixture was poured into water (1000 ml) and extracted into ethyl acetate. The combined extracts were washed with water, dried (Na2SO4) and evaporated. The residual oil was purified on the biotage eluting with light petroleum (40-60° C.), and then light petroleum (40-60° C.)-ether (9:1). The appropriate fractions were evaporated to give the title compound (18 g) LCMS RT=4.34 min.

Workup

  1. extractionextracted into ethyl acetate
  2. washThe combined extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residual oil was purified on the biotage
  6. washeluting with light petroleum (40-60° C.)
  7. customlight petroleum (40-60° C.)-ether (9:1)
  8. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-c16e8c282b58499888fb8b4f7ff19c1b
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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