Heptane, 1 bromo 2 fluoro

Heptane, 1-bromo-2-fluoro, 46,10 Heptanoic acid, 2-fluoro-, 46,37 2-Heptanone, 47, 89 4-Heptanone, 47, 75 Heptanoyl fluoride, 46, 6... 

Fluoro-4-iodoaniline (0.00791 mol) dissolved in 10 ml THF was cooled to —78°C, then treated with 6 ml 2.0 M lithium diisopropylamide in THF/heptane/ethylbenzene, and the suspension stirred 10 minutes. The mixture was further treated with 5-bromo-2,3,4-trifluorobenzoic acid (0.00392 mol) dissolved in 15 ml THF, then stirred 18 hours at ambient temperature, and concentrated. The residue was treated with 100 ml 10% HC1 and the suspension was extracted twice with 150 ml diethyl ether, then dried using MgS04. The solution was reconcentrated and an orange solid was isolated. The solid was triturated with boiling CH2C12, then cooled. The solid was isolated by filtration, then rinsed with CH2C12, and the product isolated, mp = 200—201°C. 

Dimethyl-l-oxopropoxy)methyl 25(2a,5a,6 ) -6-Bromo-6-fluoro-3,3-dimethyl-7-oxo-4-thia-l-azabicy-clo 3.2.0 heptane-2-carboxylate (Pivaloyloxy)methyI b -Bromo-ba-fluoropenicillanate Table 9, Entry I8 Typical Procedure ... 

Likewise, l-bromopentacyclo[4.3.0.0 . 0 .0 ]nonan-9-one ethylene acetal (7) reacted with lithium metal in a mixture of tcrt-butyl alcohol and tetrahydrofuran to give pentacyclo[4.3.0.0. 0 .0 ]nonan-9-one ethylene ketal (8) in 94% yield with no cleavage of the cyclopropane ring. ° Approximately 50% ring opening occurred when e.x o-3-bromo-ex o-5-fluorotricyclo[2.2.1.0 ]heptane was exposed to tributyltin hydride and gave ex o-3-fluoro-tricyclo[2.2.1.0 ]heptane and c t/o-7-fluoronorbornene in nearly 1 1 ratio. ... 

---