3-Octanol → 3-Bromooctane

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To 8 ml (23 g, 85.3 mmol) of phosphorus tribromide was added dropwise 15 g (115.4 mmol) of 3-octanol over a 1/2 hr period. The resulting solution was heated at 100° C. (oil bath) for 2 hr, after which time the reaction mixture was cooled and poured into 200 ml ice-water which was extracted with CHCl3 (3×120 ml). The combined organic extracts were washed with 5% Na2S2O3 (2×200 ml), H2O (200 ml), sat'd aq. NaHCO3 (2×200 ml), H2O (200 ml), and sat'd aq. NaCl (200 ml), and dried over MgSO4. After the removal of the solvent under reduced pressure, the residue was distilled (bp 78°-80° C./18 Torr, lit. bp 84.4°-85.1° C./20 Torr (18)) to give 17.5 g (78.58%) of pure 3-bromooctane which exhibited C-Br band at 797 cm-1 in the IR spectrum (18). NMR(CDCl3): δ1.0 (6H, t, CH3), δ1.31 (6H, broad singlet, --CH2), δ1.75 (4H, q, ##STR13## δ3.90 (1H, m, >CHBr).

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