Nonanoic Acid → Nonanoic acid, 2-bromo-

Participants

Reaction Steps

To a mixture of nonanoic acid (20 g, 126 mmol) and bromine (24.3 g 152 mmol) was added phosphorous trichloride (5.2 g, 38 mmol) slowly over 0.5 hour. The mixture was refluxed for 3 days and then diluted with ethyl acetate (200 mL). The organic phase was washed with aqueous saturated NaHSO3 (3×), separated, dried over anhydrous sodium sulfate, and the solvent removed in vacuo to yield 27.0 g of the title compound as a brown oil. 1H NMR (CDCl3, 60 MHz) δ0.70 (m, 3H), 1.20 (m, 9H), 1.90 (m, 3H), 4.13 (m, 1H), 10.80 (br s, 1H).

Provenance & Evidence