2-Bromobutane → HCID 20394007, compound

HRID 1862861Notes

Reaction equation

HRID 1862861 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:25](Br)([CH2:27][CH3:28])[CH3:26]>CN(C)C=O>[CH:25]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1)([CH2:27][CH3:28])[CH3:26]

Participants

5

Reactant 3

HCID 65542-BromobutaneHCID 11430Potassium CarbonateHCID 53768917-Hydroxyisoflavone

Product 1

HCID 20394007HCID 20394007, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12 g of 7-hydroxy-isoflavone are boiled for 2 hours under reflux condenser with 10 g of potassium carbonate and 9 g of sec-butyl bromide in 40 ml of dimethyl formamide. On pouring the reaction mixture on water, the separated product is recrystallized from acetone, yielding 12 g of 7-sec-butyloxy-isoflavone, m.p. 87°-89° C. In a similar way, also 7-sec-butyloxy-2-methyl-isoflavone, m.p. 107°-109° C., and all the other isoflavone derivatives described in Example 7 can be prepared.

Workup

  1. additionOn pouring the reaction mixture on water
  2. customthe separated product is recrystallized from acetone

Sources & evidence

ORD record
ord-24a9b379bf9c497d81a2869e5fbf5646
Source dataset
uspto-grants-1979_09
Patent number
US04166862

Reaction notes

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