4-bromo-1-(1-bromoethyl)-2-fluorobenzene

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

Procedure: A solution of 4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride (2.483 mmol) in N,N-dimethylformamide (10 mL) was treated with potassium carbonate (7.45 mmol) and 4-bromo-1-(1-bromoethyl)-2-fluorobenzene (2.483 mmol). The reaction was stirred at room temperature for three days. The solution was diluted with water (200 mL) and was extracted three times with ethyl acetate. The organic layers were combined, washed with brine (five times), dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a yellow oil (1.01 g, 89%). MS(ES)+ m/e 411.0/412.9 [M+H]+ (bromide isotope pattern). was extracted three times with ethyl acetate washed with brine (five times) dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: A solution of 1-(4-bromo-2-fluorophenyl)ethanol (8.95 mmol) in dichloromethane (40 mL) at 0° C. was treated dropwise with a solution of phosphorus tribromide (3.58 mmol) in dichloromethane (10 mL). The reaction mixture was allowed to warm to room temperature and was stirred overnight. The solution was concentrated to a residue in vacuo. Purification of the residue by silica gel chromatography (hexanes) yielded the title compound as a clear oil (1.47 g, 58.3% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.00 (d, J=6.82 Hz, 3 H) 5.58 (q, J=7.07 Hz, 1 H) 7.47 (dd, J=8.34, 1.77 Hz, 1 H) 7.57-7.65 (m, 2 H). The solution was concentrated to a residue in vacuo Purification of the residue by silica gel chromatography (hexanes)