Diethyl Ether → 958651-12-2

Temperature

-78 °C

Bromo-3-cyclopropyl-benzene (1.0 g, 5.1 mmol) [prep.: J. Org. Chem. vol. 41, 2262-6 (1976)] was dissolved in dry THF/diethyl ether (1:1, 30 ml) under an argon atmosphere and cooled to −78° C. BuLi (1.6 M in hexanes, 3.2 ml, 5.1 mmol) was added dropwise and the reaction mixture was further stirred at low temperature for 15 min. This reaction mixture was added via cannula to a SO2 gas saturated solution of diethyl ether (20 ml) precooled to −78° C. The reaction mixture was stirred overnight at room temperature and concentrated under reduced pressure. The crude intermediate was suspended in n-hexane (4A sieves dried, 20 ml) and chilled (ice-water). A solution of sulfuryl chloride (0.3 ml, 3.6 mmol) in dry hexane (8 ml) was added dropwise to the stirred suspension and then the cold bath was removed. After 90 min at room temperature the reaction mixture was filtered (Speedex pad) and the filtrate was concentrated under reduced pressure to yield a yellow oil: 0.6 g, (67%) GC-MS: M=216.

1. customprecooled to −78° C
2. stirringThe reaction mixture was stirred overnight at room temperature
3. concentrationconcentrated under reduced pressure
4. temperaturechilled (ice-water)
5. customthe cold bath was removed
6. filtrationAfter 90 min at room temperature the reaction mixture was filtered (Speedex pad)
7. concentrationthe filtrate was concentrated under reduced pressure
8. customto yield a yellow oil

ORD record

ord-94a9bcc3299841feb1fdc0123fafc4a7

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07868030B2