Sodium Iodide → 1-(Cyclopropylmethoxy)-3-ethynylbenzene

HRID 646224Notes

Reaction equation

HRID 646224 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[CH:2].Br[CH2:11][CH:12]1[CH2:14][CH2:13]1.[I-].[Na+]>CC(C)=O.CCOCC>[CH:12]1([CH2:11][O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[CH:2])[CH:4]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 81503BromomethylcyclopropaneHCID 139144m-Ethynylphenol

Product 1

HCID 597726581-(Cyclopropylmethoxy)-3-ethynylbenzeneYield 84.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-ethynylphenol (1.18 g, 10.0 mmol) in acetone (30 mL) is added (bromomethyl)cyclopropane (1.02 mL, 10.0 mmol), sodium iodide (0.75 g, 5.0 mmol) and CS2CO3 (6.52 g, 20.0 mmol) at room temperature. After refluxing over night, the reaction mixture is cooled, diluted with Et2O (300 mL) and pass through a thin layer of silica gel. The solution is concentrated. The crude material is purified by chromatography (silica gel, EtOAc/hexane:1/99) to give the title compound (1.45 g, 84%) as an oil. MS (+) APPI: 173 (M+H)+.

Workup

  1. temperatureAfter refluxing over night
  2. temperaturethe reaction mixture is cooled
  3. concentrationThe solution is concentrated
  4. customThe crude material is purified by chromatography (silica gel, EtOAc/hexane:1/99)

Sources & evidence

ORD record
ord-19065df793eb4d768db906921d3bb54e
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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