6-bromo-1,1-difluorohexane

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-6,6-difluorohexane (Step II) to give N-[4-[4-[ethyl(6,6-difluorohexyl)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 88°-90° C. Anal. calc'd for C21H34F2N2O5S: C, 54.29; H, 7.38; N, 6.03; S, 6.90. Found: C, 54.42; H, 7.58; N, 5.74; S, 6.58.