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

HRID 1362312Notes

Reaction equation

HRID 1362312 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-1d9f9805d24a4b2dbe74d73868aec59e
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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