Dichlorodiphenylmethane → 4-Bromo-7-methoxy-2,2-diphenyl-1,3-benzodioxole

Reaktionsgleichung

[Br:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:4]([OH:5])[C:3]=1[OH:11].[C:12]1([C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(Cl)Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>>[Br:1][C:2]1[C:3]2[O:11][C:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:5][C:4]=2[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1

Komponenten

Edukt 3

HCID 16327Dichlorodiphenylmethane

HCID 516892Sodium Bicarbonate

HCID 37058743-Bromo-6-methoxybenzene-1,2-diol

Produkt 1

HCID 227343704-Bromo-7-methoxy-2,2-diphenyl-1,3-benzodioxole

Versuchsvorschrift

3-Bromo-6-methoxycatechol (3.87 g) and diphenyl-dichloromethane (4.61 g) were heated at 170° C. with stirring without a solvent. After being allowed to stand for cooling, a saturated aqueous solution of sodium bicarbonate was added to the mixture, followed by extraction with ether. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was triturated with methanol to give Compound IIbl-a (4.7 g, 69%) as a white solid.