Dimethylformamide → 6-(4-Vinylbenzyloxy)bromohexane

HRID 417757Notes

Reaction equation

HRID 417757 reaction equation
CN(C=O)C.[H-].[Na+].[CH:8]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1)=[CH2:9].[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Br>O>[CH:8]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][O:15][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][Br:18])=[CH:12][CH:11]=1)=[CH2:9]

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 2735162(4-Vinylphenyl)methanol

Product 1

HCID 578645336-(4-Vinylbenzyloxy)bromohexaneYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A DMF suspension (5 ml) of sodium hydride (50% in oil, 240 mg, 5.0 mmoles) was cooled to 0° C. under an argon atmosphere, and a DMF (1 ml) solution of 1.34 g of 4-vinylbenzyl alcohol (10 mmoles) was added. The reaction mixture was agitated for fifteen minutes, and a DMF solution (3 ml) of 3.66 g of 1,6-dibromohexane (15 mmoles) was added over at least five minutes. The reaction mixture was agitated at room temperature for three hours. Fifteen milliliters of water was added to the reaction solution while cooling using ice, and the solution was agitated for five minutes. The solution was extracted using ethyl acetate (2×40 ml). The combined organic layers were washed using 15 ml of saturated aqueous saline solution and dried using anhydrous sodium sulfate. Upon filtration and concentration, 4.11 g of the residue was purified using silica gel column chromatography (70 g silica gel, 20:1 hexane/Et2O) and 1.72 g of 6-(4-vinylbenzyloxy)bromohexane (5.8 mmoles, 58%) was obtained in the form of an oily substance.

Workup

  1. stirringThe reaction mixture was agitated at room temperature for three hours
  2. temperaturewhile cooling
  3. stirringthe solution was agitated for five minutes
  4. extractionThe solution was extracted
  5. washThe combined organic layers were washed
  6. customdried
  7. filtrationUpon filtration and concentration, 4.11 g of the residue
  8. customwas purified

Sources & evidence

ORD record
ord-6809c694e9f747359c1544392d1414b4
Source dataset
uspto-grants-2012_01
Patent number
US08092720B2

Reaction notes

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