2-Iodophenol → 1-But-2-enyloxy-iodobenzene

HRID 2097058Notes

Reaction equation

HRID 2097058 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[H-].[Na+].[CH2:11](Br)[CH:12]=[CH:13][CH3:14]>CN(C=O)C>[CH2:11]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[I:1])[CH:12]=[CH:13][CH3:14]

Participants

5

Reactant 3

HCID 107842-IodophenolHCID 24758Sodium hydrideHCID 1224142-Butene, 1-bromo-

Product 1

HCID 614000581-But-2-enyloxy-iodobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

An ice-cold solution of 2-iodophenol (10.0 g, 45.4 mmol) in DMF (100 mL) was added dropwise to a solution of NaH (2.16 g, 90.8 mmol) in DMF at 0° C. Crotylbromide (7.97 g, 59.0 mmol) was then added. The mixture was warmed to room temperature and stirred overnight. The reaction was quenched with water (50 mL) and the mixture was extracted with CH2Cl2 (3×). The combined organics were washed with brine and dried over Na2SO4 to give the title compound (12.2 g, 99%) as a yellow oil: 1H NMR (500 MHz, DMSO-d6) δ 7.76 (dd, J=7.8, 1.5 Hz, 1H), 7.27-7.22 (m, 1H), 6.80 (dd, J=8.4, 1.2 Hz, 1H), 6.70-6.65 (m, 1H), 5.95-5.80 (m, 1H), 5.75-5.65 (m, 1H), 4.55-4.45 (m, 2H), 1.76-1.70 (m, 3H); ESI MS m/z 275 (M+H)+.

Workup

  1. customThe reaction was quenched with water (50 mL)
  2. extractionthe mixture was extracted with CH2Cl2 (3×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-979469b3b73743618875b15323e73d58
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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