تفاعل #302854

ord-54020c6efa304eb485750fadda8bc881

معادلة التفاعل

COc1ccc(C(=O)CC(=O)c2cc(Br)ccc2O)cc1
compound 14
COc1ccc(C(=O)CC(=O)c2cc(Br)ccc2O)cc1
1-(5-bromo-2-hydroxyphenyl)-3-(4-methoxyphenyl)propan-1,3-dione
O=S(=O)(O)O
sulfuric acid
COc1ccc(-c2cc(=O)c3cc(Br)ccc3o2)cc1
compound 15
COc1ccc(-c2cc(=O)c3cc(Br)ccc3o2)cc1
6-bromo-4′-methoxyflavone

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةwas heated
  2. 2
    درجة الحرارةto reflux for 1 hour
  3. 3
    أخرىwas returned to room temperature
  4. 4
    workup.ADDITIONice pieces were then added to the reaction solution
  5. 5
    ترشيحThe precipitated crystal was collected by filtration

الإجراء التجريبي

A mixed solution consisting of compound 14 (2.67 g, 7.65 mmol), concentrated sulfuric acid (0.78 ml), and acetic acid (40 ml) was heated to reflux for 1 hour. The temperature of the resultant was returned to room temperature, and ice pieces were then added to the reaction solution. The precipitated crystal was collected by filtration, so as to obtain a product of interest, 6-bromo-4′-methoxyflavone (compound 15). Yield: 2.01 g (yield constant: 79.4%) 1H NMR (300 MHz, CDCl3) δ8.35 (s, 1H), 7.87 (d, J=9.0 Hz, 2H), 7.77 (d, J=9.0 Hz, 1H), 7.45 (d, J=9.3 Hz, 1H), 7.03 (d, J=9.0 Hz, 2H), 6.75 (s, 1H), 3.90 (s, 3H).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08192717B2uspto-grants-2012_06