Hydrochloric Acid → HCID 433777, Verbindung

Magnesium turnings (1.22 g) and iodine (1 crystal) were added to dry tetrahydrofuran (10 ml) under a nitrogen atmosphere. A solution of 3-fluoro-4-trifluoromethoxybromobenzene (12.95 g) in dry tetrahydrofuran (30 ml) was placed in a dropping funnel. About 10% of this was added to the mixture, and the Grignard reaction began immediately. The rest of the mixture was added dropwise with stirring, and the temperature rose until the solvent was at reflux. After the addition was complete the mixture was allowed to cool, then a solution of methyl-2-(2H-tetrazol-2-yl)propionate (3.9 g) in dry tetrahydrofuran (10 ml) was added with stirring. An exotherm was noted, and the reaction was allowed to stir at room temperature for 30 minutes. The mixture was then poured into water (100 ml). The mixture was acidified by adding 3M hydrochloric acid (100 ml) and then extracted with diethyl ether (3×100 ml). The combined ethereal extracts were dried over anhydrous sodium sulphate and evaporated to a brown oil (10 g). This was chromatographed on silica gel eluting with 4:1 hexane/ethylacetate to give an oil (1.85 g).

1. additionAbout 10% of this was added to the mixture
2. customthe Grignard reaction
3. additionThe rest of the mixture was added dropwise
4. temperatureat reflux
5. additionAfter the addition
6. temperatureto cool
7. stirringwith stirring
8. stirringto stir at room temperature for 30 minutes
9. extractionextracted with diethyl ether (3×100 ml)
10. dry with materialThe combined ethereal extracts were dried over anhydrous sodium sulphate
11. customevaporated to a brown oil (10 g)
12. customThis was chromatographed on silica gel eluting with 4:1 hexane/ethylacetate

ORD-Eintrag

ord-1880e1dc11c34a4d82ef539c375337b5

Quelldatensatz

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04829074