Phosphorus tribromide → 2-(Bromomethyl)-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

A solution of 2-hydroxymethyl-1,2,3,4-tetrahydronaphthalene (2.28 g, 14.0 mmol) in 100 ml of CH2Cl2 was treated with PBr3 (1.28 g, 4.73 mmol) at 0° C. The mixture was stirred at room temperature for 72 hours then poured onto 100 g of ice. The organic layer was isolated, washed with 10% K2CO4 aqueous solution, H2O , sat'd brine, and then dried over Na2SO4. After filtration and removal of solvent, the residue was purified by chromatography (SiO2, EtOAc:hexane, 1:10) to give a colorless oil (1.33 g, 41.6%); 1H NMR (CDCl3, 300 MHz) δ 1.55 (m, 1H), 2.11 (m, 1H), 2.11 (m, 2H), 2.58 (dd, J1 =16.2 Hz, J2 =10.2 Hz, 1H), 2.80-3.10 (m, 3H), 3.45 (d, J=6.3 Hz, 2H), 7.10 (m, 4H).

Provenance & Evidence