Tributylvinyltin → HCID 15017665, compound

Temperature

98 °C

To a solution of 2,4,5-trifluoro-3-trifluoro methanesulfonyl benzoic acid, methyl ester (22.0 g, 0.065 mol) in dioxane (100 mL) was added tri-n-butyl vinyl tin (21.6 g, 0.068 mol), lithium chloride (16.7 g, 0.37 mL) 2,6-di-t-butyl-4-methylphenol (0.08 g) and palladium-tetra-triphenyl phosphine (1.1 g). The mixture was heated at 98° C. for 12 hours, cooled, diluted with ether and filtered through celite. The ether layer was concentrated and the resulting residue suspended in hexane and filtered. The filtrate was concentrated to a yellow oil which was immediately dissolved in methanol (250 mL) and 1N sodium hydroxide (150 mL). The mixture was stirred at room temperature for 4 hours, diluted with water and ether. The aqueous layer was acidified (pH~2) with 6N HCl and extracted with methylene chloride. The organic layer was dried and concentrated to provide the desired product 9.6 g, 77%); mp 108°-110° C.

1. temperaturecooled
2. filtrationfiltered through celite
3. concentrationThe ether layer was concentrated
4. filtrationfiltered
5. concentrationThe filtrate was concentrated to a yellow oil which
6. dissolutionwas immediately dissolved in methanol (250 mL)
7. additiondiluted with water and ether
8. extractionextracted with methylene chloride
9. customThe organic layer was dried
10. concentrationconcentrated

ORD record

ord-e537abfc771747e88b3973f7563c73e1

Source dataset

uspto-grants-1991_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05047538