6-Bromo-2-naphthalenol → 6-((Trimethylsilyl)ethynyl)naphthalen-2-ol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-bromonaphthalen-2-ol (3.8 g, 17.04 mmol), ethynyltrimethylsilane (7.08 ml, 51.1 mmol), (PPh3)2PdCl2 (1.79 g, 2.56 mmol), TEA (12 ml, 85 mmol) in THF (12 ml) was added copper(I) iodide (0.324 g, 1.70 mmol). The resulting mixture was heated at 70° C. in oil bath overnight and cooled. To the mixture was added silica gel (40 g) and the resulting mixture was dried on vacuum. The gel powder was loaded on a silica gel column, eluted with DCM to provide compound 110A.

Provenance & Evidence