1-Ethynyl-4-(trifluoromethyl)benzene → (4-{3-[3-Bromo-5-(4-trifluoromethyl-phenylethynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester

関与物質

役割	名称	HCID	仕込み量
反応物	1-Ethynyl-4-(trifluoromethyl)benzene	HCID 4348295	—
反応物	{4-[3-(3,5-Dibromo-phenyl)-prop-2-ynyloxy]-2-methyl-phenoxy}-acetic acid methyl ester	HCID 67157962	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
触媒	HCID 178418476	HCID 178418476	—
溶媒	Dimethylformamide	HCID 6228	—
溶媒	Triethylamine	HCID 8471	—
生成物	(4-{3-[3-Bromo-5-(4-trifluoromethyl-phenylethynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester	HCID 67159034	—

反応条件

温度	75 °C

反応手順

A mixture of 1-ethynyl-4-trifluoromethyl-benzene (149 mg, 0.88 mmol), {4-[3-(3,5-dibromo-phenyl)-prop-2-ynyloxy]-2-methyl-phenoxy}-acetic acid methyl ester (412 mg, 0.88 mmol, intermediate 2), Pd(PPh3)2Cl2 (101 mg, 0.088 mmol), CuI (46 mg, 0.246 mmol) in dry DMF (2 ml) and triethylamine (2 ml) was heated in a microwave own for 20 min. at 75° C. in a sealed tube. The reaction mixture was filtered through Decalite and the filtrate was evaporated. The residue was purified on column chromatography using methylene chloride/heptanes mixtures to give (4-{3-[3-bromo-5-(4-trifluoromethyl-phenylethynyl)-phenyl]-prop-2-ynyloxy}-2-methyl-phenoxy)-acetic acid methyl ester in 94 mg (19%) yield.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07943612B2
出典データセット	uspto-grants-2011_05
ORD ID	ord-b0cc093ae5c740848a088bded0eef0e6
出典メモ	uspto-grants-2011_05