1-Bromohexane → 1,4-Dibromo-2,5-bis(hexyloxy)benzene

HRID 471360Notes

Reaction equation

HRID 471360 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:9]=[C:8]([OH:10])[C:7]([Br:11])=[CH:6][C:5]=1[OH:12].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CS(C)=O>[Br:3][C:4]1[CH:9]=[C:8]([O:10][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]([Br:11])=[CH:6][C:5]=1[O:12][CH2:8][CH2:9][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 14797Potassium HydroxideHCID 2809452,5-Dibromohydroquinone

Product 1

HCID 167262041,4-Dibromo-2,5-bis(hexyloxy)benzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of KOH powder (10.47 g, 186.6 mmol) in dried DMSO (360 mL) was degassed under vigorous stirring for 1 h. 2,5-dibromo-1,4-dihydroxybenzene (5 g, 18.66 mol) and 1-bromohexane (5.8 mL, 41.06 mmol) were added and stirred for 12 h. The solution was concentrated and precipitated in water, filtered, washed with methanol. The product was recrystallized in ethanol, dried in vacuo (4.518 g, 55.5%). 1H NMR(300 MHz, CDCl3): δ 7.08 (s, 2H), 3.95 (t, 4H), 1.8 (m, 4H), 1.49 (m, 4H). 1.37 (m, 8H), 0.9 (t, 6H).

Workup

  1. customwas degassed
  2. stirringstirred for 12 h
  3. concentrationThe solution was concentrated
  4. customprecipitated in water
  5. filtrationfiltered
  6. washwashed with methanol
  7. customThe product was recrystallized in ethanol
  8. customdried in vacuo (4.518 g, 55.5%)

Sources & evidence

ORD record
ord-ac65d9e1b72446fe9a359217dd2cf247
Source dataset
uspto-grants-2014_01
Patent number
US08633140B2

Reaction notes

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