Dichloromethane → 1-(5-Chloro-2-methoxy-4-methyl-3-vinylphenyl)ethanone

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 5233012	—
Reactant	1-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone	HCID 86666759	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-(5-Chloro-2-methoxy-4-methyl-3-vinylphenyl)ethanone	HCID 86677749	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone (2.6 g, 9.5 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (1.9 mL, 11 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (400 mg, 0.5 mmol) and potassium carbonate (4.0 g, 29 mmol) in 1,4-dioxane (60 mL), and water (30 mL). The resulting mixture was heated at 80° C. for 3 hours. The mixture was cooled to room temperature and extracted with ethyl acetate. Purification on a silica gel using ethyl acetate in hexanes (0-20%) gave the desired compound, 2.0 g, 94%. LCMS calculated for C12H14ClO2 (M+H)+: m/z=225.1; found: 225.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09199982B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-35f885b0fcc24315b8ba73327b96f2d5
Source note	uspto-grants-2015_12