تفاعل #2845

ord-3997d852565a4edcadde399de94e54e4

معادلة التفاعل

N#Cc1cc(CO)cs1
4-hydroxymethyl-thiophene-2-carbonitrile
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenyl phosphine
BrC(Br)(Br)Br
carbon tetrabromide
N#Cc1cc(CBr)cs1
title compound
المردود 95.8%
N#Cc1cc(CBr)cs1
4-Bromomethyl-thiophene-2-carbonitrile
المردود 95.8%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحthe solution is filtered
  2. 2
    تركيزconcentrated
  3. 3
    أخرىThe crude product is purified by column chromatography
  4. 4
    غسيلeluting with gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

الإجراء التجريبي

To a solution of 4-hydroxymethyl-thiophene-2-carbonitrile (10 g, 72 mmol), in 360 mL of THF is added triphenyl phosphine (18.3 g, 76 mmol) and carbon tetrabromide (25 g, 76 mmol). After 3 h, the solution is filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes to afford the title compound (14 g, 69 mmol) as a white solid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05731315uspto-grants-1998_03