Azide → HCID 20278120, compound

The reaction mixture was distilled at ca. 65 mmHg pressure until 70 g of condensate had been collected; further distillate when examined by g.l.c. (2 m silicone, 50°) contained none of the required azide. The distillate was added to ice water (500 ml), shaken, and the lower organic layer (17.1 g) separated, shaken with an excess of aqueous sodium bicarbonate solution, then with water, and dried (Na2SO4). The washings were added to the ice-water layer, which was then extracted three times with ether. The combined ether extracts were washed with an excess of aqueous sodium bicarbonate solution, then with water and dried. The ether was removed to leave a residue of the azide concentrate (13.0 g). The azide was not isolated in the pure state, but as a precaution was handled diluted with ether, olefin and unchanged bromo-compound. The separated organic layer (17.1 g, above) by g.l.c. (2 m silicone, 50°) contained 1,1,1-trifluoro-3-methyl-2-butene (27%), 3-bromo-1,1,1-trifluoro-3-methylbutane (17%) and the azide. The product yields estimated by g.l.c. were 3-azide-1,1,1-trifluoro-3-methylbutane (10.0 g, 15%), 1,1,1-trifluoro-3-methyl-2-butene (27.5 g, 55%), and 3-bromo-1,1,1-trifuloro-3-methylbutane unreacted (4.4 g, 5%). The remaining material was partly accounted for as 1,1,1-trifluoro-3-methyl-2-butene in the ether distillate.

1. distillationThe reaction mixture was distilled at ca. 65 mmHg pressure until 70 g of condensate
2. customhad been collected
3. custom(2 m silicone, 50°)
4. additionThe distillate was added to ice water (500 ml)
5. customthe lower organic layer (17.1 g) separated
6. stirringshaken with an excess of aqueous sodium bicarbonate solution
7. dry with materialwith water, and dried (Na2SO4)
8. additionThe washings were added to the ice-water layer, which
9. extractionwas then extracted three times with ether
10. washThe combined ether extracts were washed with an excess of aqueous sodium bicarbonate solution
11. dry with materialwith water and dried
12. customThe ether was removed
13. customto leave a residue of the azide
14. concentrationconcentrate (13.0 g)
15. customThe azide was not isolated in the pure state
16. customThe product yields

ORD record

ord-d0bc15f447bd4ddbaea41c7375d9a12d

Source dataset

uspto-grants-1985_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04524152