1,3,5-tribromobenzene (3.01 g, 9.6 mmol) in diethyl ether (80 mL) was
cooled to -78°C followed by the addition of one equivalent of n-BuLi
dropwise (2.5 M, 3.8 mL). The reaction was stirred for 30 minutes then
DMF (740 µL, 9.6 mmol) was added dropwise to the reaction and stirred at
-78°C for one hour. The vessel was then placed in an ice bath and
stirred for 30 minutes. A 10% HCl solution (100 mL) was added to quench
the reaction followed by CHCl3 (150 mL). The organic layer was collected and the aqueous layer washed with CHCl3 (80 mL). The organic layers where combined and dried over MgSO4
and the solvent removed. The crude product was purified by column
chromatography eluting with 10% EtOAc in hexanes. Spectral data for the
title compound was not reported in the literature reference. Yield: 1.93
g of the title compound (77%). 1H NMR (CDCl3, 300 MHz): δ = 9.90 (s, 1H), 7.92 (d, 2H), 7.60 (s, 1H); 13C NMR (CDCl3, 75 MHz) δ = 189.3, 139.7, 139.0, 131.37, 124.1; GC-MS [M+H]+ 262.8709, calcd 262.8707
