2-Iodophenol → HCID 66967196, compound

HRID 2097063Notes

Reaction equation

HRID 2097063 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[H-].[Na+].Br[CH2:12][CH:13]=[CH:14][CH2:15][CH3:16]>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:12][CH:13]=[CH:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 107842-IodophenolHCID 24758Sodium hydrideHCID 1407151-Bromo-pent-2-ene

Product 1

HCID 66967196HCID 66967196, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

An ice-cold solution of 2-iodophenol (6.00 g, 272 mmol) in DMF (100 mL) was added dropwise to a solution of NaH (1.30 g, 54.4 mmol) in DMF. 1-Bromo-pent-2-ene (4.87 g, 327 mmol) was then added. The mixture slowly warmed to room temperature 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 (8.50 g, 99%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.75 (dd, J=7.5, 1.2, Hz, 1H), 7.36-7.30 (m, 1H), 6.98 (d, J=8.1 Hz, 1H), 6.76-6.71 (m, 1H), 6.01-5.89 (m, 1H), 5.67 (t, J=5.7 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 2.08 (t, J=7.5 Hz, 2H),

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-36c8d4a964864377916c8fa723bee90d
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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