p-Fluoronitrobenzene → HCID 69812241, compound

Participants

Reaction Steps

On reaction of 1-fluoro-4-nitro-benzene and 3,3,3-trifluoro-2-(tetrahydro-pyran-2-yloxy)-propan-1-ol according to the procedure described in example 33 i) there was obtained 2-[2,2,2-trifluoro-1-(4-nitro-phenoxymethyl)-ethoxy]-tetrahydro-pyran. This compound was then treated with THF/1N HCl (20 min RT) to take off the tetrahydropyranyl protecting group and alkylated with methyl iodide in DMF and with NaH as a base at RT (2 h) to give 1-nitro-4-(3,3,3-trifluoro-2-methoxy-propoxy)-benzene, which was then hydrogenated as described in example 33 ii) to give the desired compound, (rac)-4-(3,3,3-trifluoro-2-methoxy-propoxy)-phenylamine.

Provenance & Evidence