4-(bromomethyl)heptane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of sodium nitrite (30.6 g, 0.43 mol) in DMSO (700 ml) was added 1-bromo-2-propylpentane (49 g, 0.254 mol). The mixture was stirred overnight at room temperature and poured into ice water (700 g). The mixture was extracted with ether (4×250 ml), the organic layers were combined, washed with water (2×500 ml), brine (500 ml), dried and concentrated in vacuo to furnish 37.4 g (93%) of 1-nitro-2-propylpentane which was 85% pure based on 1H NMR data. The mixture was extracted with ether (4×250 ml) washed with water (2×500 ml), brine (500 ml) dried concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phosphorus tribromide (33.3 g, 0.123 mol) was added dropwise to 2-propyl-1-pentanol (40 g, 0.307 mol) at −10° C. to maintain the temperature below 0° C. and the mixture was stirred overnight at room temperature. The reaction mixture was heated at 100° C. for 1 h, cooled to room temperature, and poured into ice water (250 ml). The organic layer was separated, washed with conc. H2SO4 (25 ml) followed by saturated K2CO3 (25 ml), dried and distilled in vacuo (80° C./15 mm Hg) to furnish 40 g (83%) of 1-bromo-2-propylpentane. to maintain the temperature below 0° C. The reaction mixture was heated at 100° C. for 1 h cooled to room temperature The organic layer was separated washed with conc. H2SO4 (25 ml) dried distilled in vacuo (80° C./15 mm Hg)