Water → 7-(Iodomethyl)bicyclo[4.2.0]octa-1,3,5-triene

HRID 2372742Notes

Reaction equation

HRID 2372742 reaction equation
C1(C)C=CC(S(O[CH2:11][C:12]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH:13]=2)(=O)=O)=CC=1.[I-:21].[Na+].O>CC(C)=O>[I:21][CH2:11][CH:12]1[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 19886368Benzocyclobuten-1-ylmethyl para-toluenesulfonate

Product 1

HCID 27630237-(Iodomethyl)bicyclo[4.2.0]octa-1,3,5-trieneYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6 g of benzocyclobuten-1-ylmethyl para-toluenesulfonate (prepared according to the process described in J.A.C.S., (1975), 154, p. 347) are mixed with 6.2 g of sodium iodide in 85 ml of acetone. The reaction medium is brought to reflux for 8 hours, then introduced into 150 ml of water and extracted several times with ethyl ether. The organic phase is then washed with normal sodium thiosulfate solution, dried over anhydrous magnesium sulfate and concentrated to obtain the expected compound in the form of an oil.

Workup

  1. temperatureto reflux for 8 hours
  2. extractionextracted several times with ethyl ether
  3. washThe organic phase is then washed with normal sodium thiosulfate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f06c824f8ecf4236a1a80ef07203edaa
Source dataset
uspto-grants-1992_03
Patent number
US05100902

Reaction notes

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