Sodium Carbonate → HCID 19022411, compound

Temperature

0 °C

To a solution, cooled to 0° C., of 16.5 g of 2,2-di-methyl-5-(methylsulphinyl)-1,3-benzodioxol and 6.2 g of pyridine in 230 ml of methylene chloride, there were added in succession 5.43 g of bromine and 12.1 g of N-bromosuccin-imide. The reaction mixture was stirred at 0° C. for 3 hours and then at 20° C. for a further 12 hours. The orange colored solution was cooled to 0° C., treated with 40 ml of 1M aqueous sodium sulphite solution and the pH of the mixture was adjusted to 7 by the addition of 17% aqueous sodium carbonate solution. After stirring for 10 minutes, the phases were separated. The organic phase was washed in succession with 50 ml of 1N aqueous hydrochloric acid, 50 ml of 5% sodium hydrogen carbonate solution and 3 times with 100 ml of water each time, dried over sodium sulphate and evaporated in a vacuum. The residue was chromatographed on silica gel, with elution being carried out with ethyl acetate/hexane (1:2, v/v). After crystallization from acetone/water, there was obtained 5-[(bromomethyl)-sulphinyl]-1,3-benzodioxol as white crystals having a melting point of 88°-89° C.

1. waitat 20° C. for a further 12 hours
2. temperatureThe orange colored solution was cooled to 0° C.
3. stirringAfter stirring for 10 minutes
4. customthe phases were separated
5. washThe organic phase was washed in succession with 50 ml of 1N aqueous hydrochloric acid, 50 ml of 5% sodium hydrogen carbonate solution and 3 times with 100 ml of water each time
6. dry with materialdried over sodium sulphate
7. customevaporated in a vacuum
8. customThe residue was chromatographed on silica gel, with elution
9. customAfter crystallization from acetone/water

ORD record

ord-cf34d0d49c574bff973a07501e87f36e

Source dataset

uspto-grants-1992_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05138066