1-bromo-7-fluoroheptane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to Procedure B (Example 17, Step IV) a stirred mixture of N-[4-[4-(ethylamino)-1-hydroxybutyl]phenyl]methanesulfonamide (Example 7, Step II) and sodium bicarbonate in acetonitrile was allowed to react with 1-bromo-7-fluoroheptane (Step II) to give N-[4-[4-[ethyl(7-fluoroheptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide, a compound of Formula I'. A mixture of this compound and 0.5 equivalents of fumaric acid was crystallized from acetone to give the titled product, mp 137°-138° C. Anal. calc'd for C22H37N2O5S: C, 57.36; H, 8.10; N, 6.08; S, 6.96. Found: C, 57.34; H, 8.08; N, 6.03; S, 6.95.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g (20 mmol) of 1-bromo-7-fluoroheptane was dripped into a mixture of 0.5 g of magnesium (21 mmol) and 50 ml of THF to obtain Grignard's reagent. This reagent was then dripped into a 50 ml THF solution of 4.9 g (20 mmol) of 4-(4-chloro-4-silacyclohexyl) -1.2-difluorobenzene to obtain 4-(4-(7-fluoroheptyl)-4-silacyclohexyl)-1,2-difluorobenzene. to obtain Grignard's reagent