Propargyl bromide → HCID 12073547, compound

To a solution of (2-bromo-5-methylphenylthio)ethoxymethane-1-thione (80.23 g, 275 mmol) in ethanol-THF (2/1) (420 ml), a solution of propargyl bromide (49.13 g, 413 mmol) in ethanol (140 ml) was slowly added dropwise in an ice bath and stirred in an ice bath for 20 minutes. Furthermore, while keeping the mixture in the ice bath, a solution of N,N-dimethylethylenediamine (48.48 g, 550 mmol) in ethanol (275 ml) was added dropwise over 15 minutes. The mixture was kept in the ice bath for 20 minutes, and removed from the ice bath and left at room temperature for 1 hour, followed by further stirring at 30° C. in an oil bath for 2 hours. To a separatory funnel that contained 2N aqueous hydrochloric acid (600 ml) and hexane (500 ml), the reaction mixture was added and extracted as it was. The aqueous phase was extracted with hexane (300 ml), and the organic phase combined was washed with 1N aqueous hydrochloric acid (200 ml). Then, after washing with water (200 ml×2 times), it was dried on magnesium sulfate. The solvent was evaporated to obtain 1-bromo-4-methyl-2-(prop-2-inylthio)benzene (62.35 g, 259 mmol). The yield was 94%.

1. customremoved from the ice bath
2. waitleft at room temperature for 1 hour
3. stirringby further stirring at 30° C. in an oil bath for 2 hours
4. customTo a separatory funnel that contained
5. addition2N aqueous hydrochloric acid (600 ml) and hexane (500 ml), the reaction mixture was added
6. extractionextracted as it
7. extractionThe aqueous phase was extracted with hexane (300 ml)
8. washthe organic phase combined was washed with 1N aqueous hydrochloric acid (200 ml)
9. washThen, after washing with water (200 ml×2 times), it
10. customwas dried on magnesium sulfate
11. customThe solvent was evaporated

ORD record

ord-8a0902054bde4af0b4eab9d1aa484642

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06774245B2