Phosphorus tribromide → HCID 69022121, compound

Participants

Reaction Steps

To an ice-cold solution of 5-hydroxymethylindole-1-carbamic acid tert-butyl ester (0.51 g, 2.1 mmol) in 4:1 Et2O/CH2Cl2 (4 mL) was added PBr3 (0.2 mL, 2.2 mmol), and the reaction mixture was stirred for 40 min. The reaction mixture was diluted with CH2Cl2, washed a saturated solution of NaHCO3 (3×10 mL), dried (Na2SO4), filtered, and the solvent was removed under reduced pressure to provide 5-bromomethyl-indole-1-carbamic acid tert-butyl ester as a yellow solid (0.59 g, 93%). 1H NMR (300 MHz, CDCl3) δ 8.07 (d, J=9 Hz, 1H), 7.68-7.62 (m, 2H), 7.33 (d, J=9 Hz, 1H), 6.60 (s, 1H), 4.68 (s, 2H), 1.67 (s, 9H).

Provenance & Evidence