Water → 6-Bromohexyl 4-(3-bromophenyl)butyl ether

HRID 2117667Notes

Reaction equation

HRID 2117667 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.O>[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][Br:13])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 123681,6-DibromohexaneHCID 218954894-(3-Bromophenyl)butan-1-ol

Product 1

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

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

A stirred mixture of 4-(3-bromophenyl)butan-1-ol (18 g) and 1,6 dibromohexane (48 ml) in 50% aq. sodium hydroxide (500 ml) with tetrabutylammonium bromide (1.5 g) was stirred for 2 d at 20°. The mixture was poured into water (1000 ml) and extracted into ethyl acetate (3×500 ml). The combined extracts were washed with water (1000 ml), dried (Na2SO4). The solvent was removed in-vacuo and the residual oil was purified by flash chromatography (500 g) using dichloromethane as eluent, changing to light petroleum (40-60°)-diethyl ether (9:1) to give the title compound (18 g). LCMS RT=4.34 min.

Workup

  1. extractionextracted into ethyl acetate (3×500 ml)
  2. washThe combined extracts were washed with water (1000 ml)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed in-vacuo
  5. customthe residual oil was purified by flash chromatography (500 g)

Sources & evidence

ORD record
ord-cb2909c49d0147308bbe6945d8f4c80a
Source dataset
uspto-grants-2008_10
Patent number
US07442719B2

Reaction notes

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