1-Bromododecane → Benzene, 1-(dodecyloxy)-4-iodo-

HRID 1176162Notes

Reaction equation

HRID 1176162 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.Cl>[CH2:21]([O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

Participants

7

Reactant 3

HCID 89191-BromododecaneHCID 108944-IodophenolHCID 11430Potassium Carbonate

Product 1

HCID 10883601Benzene, 1-(dodecyloxy)-4-iodo-

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Iodophenol (3.03 g, 1.38×10−2 mol), 1-bromododecane (6.65 ml, 2.77×10−2 mol) and K2CO3 (3.81 g, 2.76×10−2 mol) were dissolved in 50 ml of dry DMF and refluxed for 3.5 h under N2. After cooling, the solution was diluted with water, 2M HCl, and extracted with CH2Cl2. The combined organic layers were washed with saturated aq. NaHCO3, water, and dried over Na2SO4. The product was chromatographed on silica gel with 3:1 hexane:CHCl3 as the eluent. Yield=5.274 g (98% based on 3.03 g of 4-iodophenol). 1H NMR (250 MHz, CDCl3): δ 7.53 (d, 2H, J=8.8 Hz, Ph), 6.67 (d, 2H, J=9.0 Hz, Ph), 3.90 (t, 2H, J=6.5 Hz, —OCH2—), 1.76 (quint, 2H, J=6.6 Hz, —OCH2CH2—), 1.13-1.48 (m, 18H, —CH2—), 0.88 (t, 3H, J=6.4 Hz, —CH3). CI MS m/z: 388.125 (M+) (calcd 388.126).

Workup

  1. temperaturerefluxed for 3.5 h under N2
  2. temperatureAfter cooling
  3. extractionextracted with CH2Cl2
  4. washThe combined organic layers were washed with saturated aq. NaHCO3, water
  5. dry with materialdried over Na2SO4
  6. customThe product was chromatographed on silica gel with 3:1 hexane

Sources & evidence

ORD record
ord-d65d56decee546a287c7f166d46f3aaa
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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