tert-Butanol → HCID 69418663, compound

Participants

Reaction Steps

A second intermediate compound, 5-Bromo-naphthalen-1-ylamine, was produced as follows: To a solution of 5-bromo-naphthalene-1-carboxylic acid (10 g, 40 mmol) in t-BuOH (150 mL) was added Et3N (13.6 mL, 80 mmol) and DPPA (10.5 mL, 48 mmol) successively. After the mixture was stirred at room temperature for 1 h, it was refluxed for 16 h. The solvent was then removed and the residue was purified by chromatography on silica gel to give (5-bromo-naphthalen-1-yl)-carbamic acid tert-butyl ester (8.4 g, 65%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.60 (d, J=6.8 Hz, 1H), 8.55 (d, J=6.6 Hz, 1H), 8.50 (d, J=6.2 Hz, 1H), 8.40 (d, J=6.4Hz, 1H), 8.20 (t, J=6.7Hz, 1H), 8.10 (t, J=6.3 Hz, 1H).

Provenance & Evidence