Bromine → 1-Bromo-3-ethyladamantane

1-Bromo-3-ethyladamantane was prepared from 1-ethyladamantane (K. Gerzon et al, J. Med. Chem., 6, 760, 1963) by stirring 0.944 grams (5.76 mmol) of 1-ethyladamantane with 10 ml of liquid bromine for 4 hours, over which time the temperature was increased to reflux. The heat was removed and after cooling, a 40 ml portion of carbon tetrachloride was added. The mixture was poured into 120 ml of ice water and enough solid sodium sulfite was added with stirring to destroy the excess bromine. The layers were separated and the aqueous phase was extracted with three portions of carbon tetrachloride. The combined extracts were washed with water, then 5% aqueous sodium bicarbonate solution, then dried over magnesium sulfate (anhydrous). Evaporation of solvent yielded a yellow liquid which was distilled to afford 1.263 grams (90.3%) of 1-bromo-3-ethyladamantane, bp 114°-115° C. (3.5 mm).

1. temperatureover which time the temperature was increased
2. temperatureto reflux
3. customThe heat was removed
4. temperatureafter cooling
5. additiona 40 ml portion of carbon tetrachloride was added
6. additionThe mixture was poured into 120 ml of ice water and enough solid sodium sulfite
7. additionwas added
8. customto destroy the excess bromine
9. customThe layers were separated
10. extractionthe aqueous phase was extracted with three portions of carbon tetrachloride
11. washThe combined extracts were washed with water
12. dry with material5% aqueous sodium bicarbonate solution, then dried over magnesium sulfate (anhydrous)
13. customEvaporation of solvent
14. customyielded a yellow liquid which
15. distillationwas distilled

ORDレコード

ord-bd1dcf3cfda6470a8a0c688b0098ec73

出典データセット

uspto-grants-1982_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04346112