1,1-Dibromoethane → HCID 12044735, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 9-benzyl-9H-Carbazol-4-ol (2.46 g, 9.00 mmol), potassium carbonate (5.11 g, 27.0 mmol), and DMF (10 mL) is added dibromoethane (3.90 mL, 45.0 mmol). The mixture is stirred at 80° C. for 4.5 h and then allowed to cool and stir the remainder of the night. The mixture is then stirred at 85° C.; after about 2 h an additional 1.0 mL of dibromoethane is added. After 5.5 h the mixture is cooled and the solvent and excess dibromoethane are removed in vacuo. The residue is partitioned between Et2O, water, and brine. The organic layers are dried over MgSO4 and taken to dryness. Chromatography on silica gel (250 mL) using EtOAc-heptane (10/90 to 20/80) to give 1.80 g (53%) after crystallization from CH2Cl2-hexane; IR (drift) 1583, 1458, 1446, 1342, 1333, 1281, 1270, 1245, 1154, 1147, 1114, 783, 753, 734, 719 cm−1; 1H NMR (CDCl3) δ3.87, 4.58, 5.51, 6.66, 7.02, 7.12, 7.2-7.4, 8.43. Anal. Calcd for C21H18BrNO: C, 66.33; H, 4.77; N, 3.68; Br, 21.01. Found: C, 66.30; H, 4.76; N, 3.62.

Provenance & Evidence