2-Iodophenol → 1-Iodo-2-((3-methylbut-2-en-1-yl)oxy)benzene

HRID 2097145Notes

Reaction equation

HRID 2097145 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[H-].[Na+].[CH3:11][C:12]([CH3:16])=[CH:13][CH2:14]Br>C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:14][CH:13]=[C:12]([CH3:16])[CH3:11]

Participants

5

Reactant 3

HCID 107842-IodophenolHCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 111089611-Iodo-2-((3-methylbut-2-en-1-yl)oxy)benzeneYield 98.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-iodophenol (3.69 g, 16.8 mmol) in THF (50 mL) is added NaH (804 mg, 33.5 mmol) portion wise and stirred for 30 min at room temperature. 3,3-Dimethylallylbromide (3.9 mL, 33.5 mmol) was added and the reaction was stirred over night at room temperature. The reaction is quenched with water (20 mL) and extracted with diethyl ether (3×25 mL), the organic layers are dried over magnesium sulfate, filtered and concentrated. The compound was purified on silica gel using 100% hexanes as the eluent to yield 4.78 g (98%) of the title compound as a pale yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J=6.0 Hz, 1H), 7.35 (t, J=9.0 Hz, 1H), 7.02 (d, J=9.0 Hz, 1H), 6.74 (t, J=9.0 Hz, 1H), 5.45 (m, 1H), 4.60 (d, J=6.0 Hz, 2H), 1.75 (2s, 6H)

Workup

  1. stirringthe reaction was stirred over night at room temperature
  2. customThe reaction is quenched with water (20 mL)
  3. extractionextracted with diethyl ether (3×25 mL)
  4. dry with materialthe organic layers are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe compound was purified on silica gel using 100% hexanes as the eluent

Sources & evidence

ORD record
ord-e74981094cf641918663bdd621632fc7
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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