1,6-Dibromohexane → 1-[(2-[(6-Bromohexyl)oxy]ethoxy)methyl]-3-nitrobenzene

HRID 2116957Notes

Reaction equation

HRID 2116957 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][O:11][CH2:12][CH2:13][OH:14])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:14][CH2:13][CH2:12][O:11][CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 121923882-[(3-Nitrophenyl)methoxy]ethanol

Product 1

HCID 468331061-[(2-[(6-Bromohexyl)oxy]ethoxy)methyl]-3-nitrobenzeneYield 68.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

2-{(3-Nitrophenyl)methoxy}ethanol (6.50 g), 1,6-dibromohexane (24.2 g) and tetrabutylammonium bromide (0.21 g) were stirred under nitrogen at 200 and treated with 50% w/v sodium hydroxide (10 ml). The mixture was stirred vigorously for 19 h before water (150 ml) was added. The product was extracted with dichloromethane (3×80 ml) and the combined organic layer was dried (Na2SO4). Solvent evaporation in vacuo gave a residue that was purified by Biotage. Elution with PE-EtOAc (1:0 then 3:1) followed by solvent evaporation in vacuo gave the title compound (8.12 g). HPLC RT=3.238 min.

Workup

  1. additionwas added
  2. extractionThe product was extracted with dichloromethane (3×80 ml)
  3. dry with materialthe combined organic layer was dried (Na2SO4)
  4. customSolvent evaporation in vacuo
  5. customgave a residue that
  6. customwas purified by Biotage
  7. washElution with PE-EtOAc (1:0
  8. custom3:1) followed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-6256413c67094e0e90bd0134cb2a6831
Source dataset
uspto-grants-2008_10
Patent number
US07439393B2

Reaction notes

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