1-Nitronaphthalene → 1-Bromo-5-nitronaphthalene

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 1-nitronaphthalene (10.0 g, 58 mmol) and FeCl3 (0.066 g, 0.41 mmol) was heated to 90° C. To the solution was added dropwise bromine (3.0 mL, 58 mmol) (no any solvent was used for this reaction). The reaction mixture was stirred at 90° C. for 2 hrs. After cooling down to room temperature, the mixture was recrystallized from ethanol to give compound A as a yellow needle crystal (7.3 g, 50%). mp 119-120° C.; 1H NMR (300 MHz, CDCl3) δ 8.44 (d, J=8.7 Hz, 1H), 8.34 (d, J=8.7 Hz, 1H), 8.13 (d, J=7.5 Hz, 1H), 7.81 (d, J=7.5 Hz, 1H), 7.56 (t, J=8.1 Hz, 1H), 7.44 (t, J=8.1 Hz, 1H); 13C NMR (75 MHz, CDCl3) δ 147.2, 133.6, 132.7, 131.8, 129.6, 126.4, 125.7, 124.6, 123.7, 123.0. EI-MS (m/z) Calcd. for C10H6BrNO2:251 (M+), Found: 251.

Herkunft & Nachweise