تفاعل #417969

ord-c78f0255ddd5448f8298883d429ea4a4

معادلة التفاعل

BrB(Br)Br
BBr3
COc1cc([N+](=O)[O-])ccc1Br
1-bromo-2-methoxy-4-nitrobenzene
O=[N+]([O-])c1ccc(Br)c(O)c1
desired compound
المردود 65.0%
O=[N+]([O-])c1ccc(Br)c(O)c1
2-bromo-5-nitro-phenol
المردود 65.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe mixture was quenched with water
  2. 2
    استخلاصextracted with ethyl acetate (3×20 mL)
  3. 3
    أخرىThe combined extracts were dried
  4. 4
    أخرىthe crude was purified by flash column chromatography

الإجراء التجريبي

BBr3 (8.58 mL of 1.0M solution, 8.6 mmol) was added to the DCM (10 mL) solution of 1-bromo-2-methoxy-4-nitrobenzene (1.0 g, 4.3 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. The mixture was quenched with water and extracted with ethyl acetate (3×20 mL). The combined extracts were dried and the crude was purified by flash column chromatography to get the desired compound as pale brown powder in 65% yield (600 mg).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08877752B2uspto-grants-2014_11