p-Chlorothiophenol → HCID 21186643, compound

Participants

Reaction Steps

In a 3 neck round bottom flask equipped for overhead mechanical stirring sodium hydride (2.03 g, 50.91 mmol, 60% oil dispersion) was rinsed free of oil with hexane (2 washes) and tetrahydrofuran (200 mL) was added followed by 4-chlorothiophenol (6.69 g, 46.28 mmol in 20 mL of tetrahydrofuran). Hydrogen gas freely evolved from the reaction. Upon cessation of hydrogen evolution, 3-trifluoromethanesulfonyloxy-8-methyl-8-azabicyclo-(3.2.1)-octane (9.5 g, 46.28 mmol in 70 mL of tetrahydrofuran) was added. The reaction was refluxed overnight, then cooled and filtered through Diatomaceous earth (with ether rinse). The filtrate was concentrated at reduced pressure and residue was taken up in ether. The organic phase was washed with water and brine, dried over calcium sulfate and concentrated to afford 8.08 g (65%) of 3-(4-chlorophenylsulfanyl)-8-methyl-8-azabicyclo-(3.2.1)-octane as a tan oil which had: NMR δ7.42-7.23 (m, 4 H), 3.22 (sym m, 1 H), 3.20-3.11 (m, 2 H), 2.24 (s, 3 H), 2.03-1.97 (m, 2 H), 1.82-1.66 (m, 4 H), 1.53 (ABq, Δv1-3=14.5 Hz, J=6.5 Hz, 2 H).

Provenance & Evidence