Diethyl Ether → 1-Bromotetradec-1-yne

A 250 ml, three-necked, round bottom flask was fitted with mechanical stirrer, thermometer, addition funnel and means for providing nitrogen atmosphere. To the flask was added 41 ml (0.10 mole) of 2.4 M butyl lithium/hexane solution and 40 ml of anhydrous ether. The resulting mixture was stirred vigorously and 17.2 g (0.090 mole) of tetradecyne was added over a period of 25 min at -10° C. After stirring at -10° to -15° C. for an additional 35 min, the reaction mixture was cooled in a Dry Ice/acetone bath. About 16.0 g (0.10 mole) of bromine was added dropwise over a period of 90 min at -60° C. to -68° C. After stirring at -40° C. for an additional 40 min, the reaction mixture was poured into 100 ml of water. The resulting mixture was extracted twice with 50 ml portions of ether. The combined ethereal layers were washed twice with 50 ml portions of sodium bicarbonate solution, dried, and concentrated, resulting in 21.9 g (80% yield) of light yellow liquid. I.R. (film/neat) in cm-1 : 2230 (C≡C), 1470 (CH2), 720 [--(CH2)n --, n≥4].

1. customA 250 ml, three-necked, round bottom flask was fitted with mechanical stirrer
2. additionthermometer, addition funnel
3. customfor providing nitrogen atmosphere
4. stirringAfter stirring at -10° to -15° C. for an additional 35 min
5. temperaturethe reaction mixture was cooled in a Dry Ice/acetone bath
6. stirringAfter stirring at -40° C. for an additional 40 min
7. extractionThe resulting mixture was extracted twice with 50 ml portions of ether
8. washThe combined ethereal layers were washed twice with 50 ml portions of sodium bicarbonate solution
9. customdried
10. concentrationconcentrated
11. customresulting in 21.9 g (80% yield) of light yellow liquid

ORD record

ord-0b8c680a2bd04430a591e01e2f84edcd

Source dataset

uspto-grants-1980_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04208501