Réaction #65240

Équation de réaction

1,2-dibromo-4,4-di(hydroxymethyl)cyclopentene

1,2-dibromo- 4,4-di (hydroxymethyl)cyclopentene

p-toluenesulfonyl chloride

→

1,2-dibromo-4,4-di(tosylmethyl)cyclopentene

Rendement 46.5%

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   Concentrationwas concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved ethyl acetate
3. 3
   Lavagewashed twice with 3% hydrochloric acid
4. 4
   SéchageThe solution was dried (Na2SO4)
5. 5
   Concentrationconcentrated in vacuo

Mode opératoire

Under nitrogen, a stirred solution of 5.7 g (19.9 mmol) of 1,2-dibromo-4,4-di(hydroxymethyl)cyclopentene (Step 5) in 50 mL of pyridine at ambient temperature was treated with 19 g (99.7 mmol) of p-toluenesulfonyl chloride. The reaction was allowed to stir overnight and was concentrated in vacuo. The residue was dissolved ethyl acetate and washed twice with 3% hydrochloric acid followed by brine. The solution was dried (Na2SO4) and concentrated in vacuo to give 5.2 g (44%) of 1,2-dibromo-4,4-di(tosylmethyl)cyclopentene (14 in Synthetic Scheme V) as a colorless semisolid: NMR (CDCl3) δ2.42 (s, 4H), 2.47 (s, 6H), 3.90 (s, 4H), 7.37 (d, J=8 Hz, 4H), 7.74 (d, J=8 Hz, 4H).

Source