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

HRID 271118Notes

Reaction equation

HRID 271118 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 resultant residue 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 resultant residue is purified by chromatography (silica gel, EtOAc/hexane: 1/99)

Sources & evidence

ORD record
ord-e8545dbd58b1427696aaa8cc0392e7f1
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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