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

HRID 2220446Notes

Reaction equation

HRID 2220446 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+].C([O-])([O-])=O.[Cs+].[Cs+]>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

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 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-6050ba02291549849330c24c5f037cd2
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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