Allyl bromide → 6338-34-7

An oven dried, two neck round bottomed flask equipped with a Teflon magnetic stir bar was charged with 3.00 g of isosorbide (20.5 mmol), 5.30 g potassium t-butoxide (47.2 mmol), and 50 mL of anhydrous DMF. This heterogeneous mixture was stirred for 30 minutes at room temperature, then brought to about 0 degrees Celsius in an ice/saturated brine bath. While stirring and under argon, 3.90 mL of allyl bromide (45.2 mmol) was added dropwise via syringe. After addition was complete, the ice bath was removed and the solution warmed to room temperature. The reaction was continued for 4 hours at room temperature under argon. After this time, the heterogeneous solution was filtered to remove potassium bromide and other solids. The filtrate was then transferred to a 250 mL boiling flask containing a Teflon stir bar, was diluted with 50 mL of methylene chloride and 50 mL of water, and vigorously stirred. The biphasic solution was poured into a 250 mL separatory funnel and the bottom organic layer removed into a 125 mL Erlenmeyer flask. This solution was then diluted with another 50 mL volume of water, the resultant biphasic solution mixed as before, and the organic phase was extracted, dried with anhydrous magnesium sulfate and concentrated in vacuo, producing a light yellow oil, 4.12 g (89%). This material was spectroscopically confirmed by GC/MS (EI), providing one signal (m/z 226.1) corresponding to (3R,3aR,6S,6aR)-3,6-bis(allyloxy)hexahydrofuro[3,2-b]furan (diallyl isosorbide, B).

1. customAn oven dried
2. customtwo neck round bottomed flask equipped with a Teflon magnetic stir bar
3. custombrought to about 0 degrees Celsius in an ice/saturated brine bath
4. stirringWhile stirring and under argon
5. additionAfter addition
6. customthe ice bath was removed
7. temperaturethe solution warmed to room temperature
8. waitThe reaction was continued for 4 hours at room temperature under argon
9. filtrationAfter this time, the heterogeneous solution was filtered
10. customto remove potassium bromide and other solids
11. additioncontaining a Teflon
12. stirringstir bar
13. additionwas diluted with 50 mL of methylene chloride and 50 mL of water
14. stirringvigorously stirred
15. additionThe biphasic solution was poured into a 250 mL separatory funnel
16. customthe bottom organic layer removed into a 125 mL Erlenmeyer flask
17. additionThis solution was then diluted with another 50 mL volume of water
18. additionthe resultant biphasic solution mixed as before, and the organic phase
19. extractionwas extracted
20. dry with materialdried with anhydrous magnesium sulfate
21. concentrationconcentrated in vacuo
22. customproducing a light yellow oil, 4.12 g (89%)

ORD record

ord-4b12964c3af745b48f82a3e02e0d669e

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290509B2