Potassium Carbonate → 1-Isopropenyl-4,5-dimethoxy-2-nitro-benzene

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Bromo-5-nitroveratrole	HCID 170968	—
Reactant	4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane	HCID 10997426	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-Isopropenyl-4,5-dimethoxy-2-nitro-benzene	HCID 59377843	28.5%

Reaction Conditions

Temperature	100 °C

Reaction Steps

1-Bromo-4,5-dimethoxy-2-nitro-benzene (6.55 g, 25.0 mmol), potassium carbonate (2 eq, 6.91 g) and tetrakis(triphenylphosphine)palladium(0) (0.125 eq, 3.61 g) were dissolved in dioxane. Isopropenylboronic acid pinacol ester (1 eq, 4.7 ml) was added and the mixture was heated to 100° C. overnight. Upon cooling the mixture was filtered through celite. The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography (gradient 9:1 to 1:1 Hexanes/Ethyl Acetate) to give 1-isopropenyl-4,5-dimethoxy-2-nitro-benzene (1.59 g, 28.5%) as a yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08153809B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-8a05b740cc2140619e5aff7f443c6dcb
Source note	uspto-grants-2012_04