Sulfuric Acid → 6-bromo-4'-methoxyflavone

HRID 215672Notes

Reaction equation

HRID 215672 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([C:8](=[O:20])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=O)[CH:7]=1.S(=O)(=O)(O)O>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:21][C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)=[CH:9][C:8]2=[O:20]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 115738361,3-Propanedione, 1-(5-bromo-2-hydroxyphenyl)-3-(4-methoxyphenyl)-

Product 1

HCID 115372566-bromo-4'-methoxyflavone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. customwas returned to room temperature
  4. additionice pieces were then added to the reaction solution
  5. filtrationThe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-54020c6efa304eb485750fadda8bc881
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

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