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3-(2-PHENYLETHYNYL)BENZOIC ACID METHYL ESTER synthesis
- Product Name:3-(2-PHENYLETHYNYL)BENZOIC ACID METHYL ESTER
- CAS Number:179244-72-5
- Molecular formula:C17H14O2
- Molecular Weight:250.29
Yield:179244-72-5 17%
Reaction Conditions:
with bis(1,5-cyclooctadiene)nickel (0);tri-tert-butylphosphine tetrafluoroborate in diethylene glycol dimethyl ether at 140; for 4 h;Sealed tube;
Steps:
Couplings with Mesylates; General Procedure B
General procedure: Carboxylate was weighed in an oven-dried 4-mL scintillation vial containing a magnetic stir bar. The vial was taken into a glovebox, and mesylate, Ni(COD)2 and PMe3HBF4 were added. Anhydrous 1,4-dioxane or diglyme was added, the vial was sealed with a Teflon-lined cap, then taken out of the glovebox, and the reaction mixture was stirred at the indicated temperature for the indicated time. The reaction mixture was cooled to room temperature and filtered through a 1.5-inch plug of silica gel, eluting with Et2O (100 mL). The filtrate was concentrated and chromatographed on a silica gel column to afford the product.
References:
Howard, Anna;Klemann, Samantha;Kolling, Sarah;Little, Katrina;Plasek, Erin;Kalyani, Dipannita [Synthesis,2019,vol. 51,# 7,p. 1603 - 1610]