Carbon tetrabromide → 1,1'-Biphenyl, 4-(3-bromopropoxy)-

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Reaction Steps

Triphenylphosphine (1.61 g, 6.14 mmol) was added to a solution of 3-(biphenyl-4-yloxy)-propan-1-ol (Example 291, Step 6) (1.00 g, 4.38 mmol) and carbon tetrabromide (1.81 g, 5.47 mmol) in CH2Cl2 (20 mL) at 0° C. The mixture was warmed to room temperature and stirred for about an hour and then extracted with ethyl acetate (50 mL). The organic layer was washed with H2O (3×50 mL) and brine (3×25 mL), and then dried (MgSO4), filtered and concentrated. The crude product was purified by silica gel column chromatography (silica gel, hexanes/ethyl acetate, 9:1) to produce 4-(3-bromo-propoxy)-biphenyl. 1H-NMR (200.15 MHz, CDCl3): d 7.57–7.29 (m, 7H), 6.98 (dd, 2H, J=6.72, 1.88), 4.45 (t, 2H, J=5.92), 3.62 (t, 2H, J=6.44), 2.34 (qn, 2H, J=5.92).

Provenance & Evidence