Boron tribromide → 3,6,3',4'-Tetrahydroxyflavone

HRID 2301351Notes

Reaction equation

HRID 2301351 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:12]4[C:17]([C:18](=[O:21])[C:19]=3[OH:20])=[CH:16][C:15]([O:22]C)=[CH:14][CH:13]=4)=[CH:9][C:4]=2[O:3]C1.B(Br)(Br)Br>>[OH:3][C:4]1[CH:9]=[C:8]([C:10]2[O:11][C:12]3[C:17]([C:18](=[O:21])[C:19]=2[OH:20])=[CH:16][C:15]([OH:22])=[CH:14][CH:13]=3)[CH:7]=[CH:6][C:5]=1[OH:1]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 18372877HCID 18372877, compound

Product 1

HCID 6675813,6,3',4'-TetrahydroxyflavoneYield 50,536,600%

Procedure

The reaction was conducted according to the same procedure as Example 57 except that 50 mg (159 pmol) of the compound obtained in Example 5 instead of the compound obtained in Example 12 and 5.0 molar equivalents of boron tribromide (BBr3) were used. Then the resulting product was separated by preparative TLC to give 23 mg of the title compound in a yield of 51%.

Workup

  1. customThen the resulting product was separated by preparative TLC

Sources & evidence

ORD record
ord-374bb4a5eb744f08b3a7cbc7eb1b3090
Source dataset
uspto-grants-2002_12
Patent number
US06500846B1

Reaction notes

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