Water → HCID 14304992, compound

HRID 477063Notes

Reaction equation

HRID 477063 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([O:25]C)[C:22]=1[O:23]C)[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:19])[C:15]=1[C:16]([OH:18])=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2.B(Br)(Br)Br.O>ClCCl>[OH:25][C:21]1[CH:20]=[C:5]([CH:4]=[C:3]([OH:2])[C:22]=1[OH:23])[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:19])[C:15]=1[C:16]([OH:18])=[O:17])=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 3

HCID 962Water2×HCID 25134Boron tribromideHCID 143049774-Oxo-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-3-carboxylic acid

Product 1

HCID 14304992HCID 14304992, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.0 g of 3',4',5'-trimethoxyflavone-3-carboxylic acid were added to 200 ml of absolute dichloromethane and reacted with 82 ml of a 1 molar boron tribromide solution in absolute dichloromethane under a nitrogen atmosphere at 0° C. The reaction mixture was stirred for twelve hours during which it was allowed to warm to room temperature. Then, for working up, water was carefully added under ice cooling, then made up to twice the volume with water and intensively stirred. The resulting 3',4',5'-trihydroxyflavone-3-carboxylic acid precipitated and was filtered out. The filter cake was washed with water several times and recrystallized from methanol. 3 g of pure 3',4',5'-trihydroxyflavone-3-carboxylic acid were obtained.

Workup

  1. stirringintensively stirred
  2. customThe resulting 3',4',5'-trihydroxyflavone-3-carboxylic acid precipitated
  3. filtrationwas filtered out
  4. washThe filter cake was washed with water several times
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ba6229479aa04f53b7f9cc7803868a3c
Source dataset
uspto-grants-1989_12
Patent number
US04886806

Reaction notes

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