Pyridine → 2-bromo-2,3-dihydro-1H-indene

Participants

Reaction Steps

To 2-indanol (Aldrich) (105 g, 0.78 mol) in pyridine (16 mL, 0.2 mol) and 340 mL of chloroform at -15° C. was added PBr3 (84 mL, 0.89 mol) over 45 min. The reaction mixture was stirred overnight at room temperature and extracted by addition of 450 mL of chloroform and 500 g of ice. The organic layer was washed twice with water, and dried over Na2SO4. The solvent was evaporated in vacuo, leaving a brown semi-solid. The product was distilled rapidly in vacuo and then fractionated to give 69 g (45%) 2-bromoindane, bp 90°-93°/3 mmHg; nD23 =1.5837.

Provenance & Evidence