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

HRID 654748Notes

Reaction equation

HRID 654748 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-055857bdb9934466a7e46a31248071d8
Source dataset
uspto-grants-1992_07
Patent number
US05134147

Reaction notes

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