تفاعل #325662

ord-65cdf4843e424619bae027e2bf1b6106

معادلة التفاعل

CC(C)(C)c1ccc([N+](=O)[O-])cc1Br
1-(tert-butyl)-2-bromo-4-nitrobenzene
C=CCCO
3-buten-1-ol
CC(C)(C)c1ccc([N+](=O)[O-])cc1C=CCCO
4-(2-tert-Butyl-5-nitro-phenyl)-but-3-en-1-ol

المذيبات

ظروف التفاعل

درجة الحرارة
120°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىwas degassed with nitrogen
  2. 2
    درجة الحرارةThe next day, the reaction mixture was cooled to RT
  3. 3
    ترشيحfiltered
  4. 4
    تركيزconcentrated in vacuo
  5. 5
    غسيلThe crude was eluted on a silica gel column with 15% to 22% EtOAc/hexanes gradient system
  6. 6
    أخرىto yield a yellow-brown oil

الإجراء التجريبي

A mix of 1-(tert-butyl)-2-bromo-4-nitrobenzene (3.652 g), TEA (5.92 ml), 3-buten-1-ol (5.48 ml), Pd(OAc)2 (32 mg), Pd(PPh3)4 (327 mg) and toluene (40 ml) was degassed with nitrogen and heated in a sealed vessel for 16 h at 120° C. The next day, the reaction mixture was cooled to RT, filtered, and concentrated in vacuo. The crude was eluted on a silica gel column with 15% to 22% EtOAc/hexanes gradient system to yield a yellow-brown oil.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08642624B2uspto-grants-2014_02