تفاعل #1519101

ord-2de18b58dc1d42b5b73d66ff38800e42

معادلة التفاعل

BrC(Br)(Br)Br
Tetrabromomethane
OCC1CC2C=CC1O2
7-oxanorborn-2-en-5-ylmethanol
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
BrCC1CC2C=CC1O2
7-oxanorborn-2-en-5-yl-methyl bromide

الكواشف

لا شيء

المذيبات

ظروف التفاعل

درجة الحرارة
0°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةto warm to room temperature
  2. 2
    أخرىThe solvent was removed under reduced pressure
  3. 3
    أخرىThe crude product was purified by flash chromatography (
  4. 4
    workup.ADDITIONa 98:2 mixture of cyclohexane and ethyl acetate)
  5. 5
    أخرى0.3 g (59% of theory) of the pure product were obtained

الإجراء التجريبي

Tetrabromomethane (1.161 g, 3.50 mmol) was added to a solution of 7-oxanorborn-2-en-5-ylmethanol (0.305 g, 2.50 mmol, from Example 2) in CH2Cl2 (12.5 ml). The solution was cooled to 0° C. and admixed with triphenylphosphine (1.836 g, 7 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 12 h. The solvent was removed under reduced pressure and the remaining solid was taken up in cyclohexane. The crude product was purified by flash chromatography (using a 98:2 mixture of cyclohexane and ethyl acetate). 0.3 g (59% of theory) of the pure product were obtained. The product was stored under cool conditions with the exclusion of light.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07612008B2uspto-grants-2009_11