Tetrahydrofuran → HCID 90410938, compound

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Reaction Steps

To the solution of 4,4′-methylene-bis(3-bromo-N,N-dimethylaniline) (2.0 g, 4.85 mmol) in anhydrous THF (50 mL), 1.4 M sec-BuLi (12.13 mmol) at −78° C. was added, and the mixture stirred for 30 min. At the same temperature, a solution of GeMe2Cl2 (1.26 g, 7.28 mmol) in anhydrous THF (15 mL) was slowly added. The mixture was warmed to room temperature and stirred for 1 h. The reaction was quenched by addition of 2 N HCl (7 ml), and the mixture neutralized with NaHCO3 and extracted with CH2Cl2. The organic layer was washed with brine and dried over Na2SO4. To this solution, the sufficient chlorinil (5 eq.) was added, and the resultant mixture stirred for 2 hours. Acetone/saturated NaHCO3 (50 mL/100 ml) were added, and the mixture stirred overnight. The mixture was then diluted with CH2Cl2 (200 mL), filtered through glass wool, and the filtrate extracted three times with methylene chloride and evaporated to dryness. The residue was purified by silica column chromatography using heptane/methylene chloride/ethyl acetate as eluent to give light yellow compound. 1HNMR (300 MHz, CD2Cl2): δ 8.32 (d, 2H), 6.7-6.90 (m, 4H), 3.20 (s, 12H, NCH3), 0.6 (d, 6H, CH3); MS (m/e): calculated 370.11. found 371.0 for [M+H]+.

Provenance & Evidence