2-[2-(4-bromophenyl)ethoxy]ethanol

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

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

Conditions: temp:145.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-[2-(4-bromophenyl)ethoxy]ethanol (10.8 g, 0.044 mol; see step (iii) above in DMF (100 mL), CuCN (7.8 g, 0.088 mol) was added and refluxed at 140 to 150° C. overnight. After removal of DMF by distillation, the reaction was quenched by the addition of water. Inorganic matter was removed by filtration and the aqueous layer was extracted with ethyl acetate (4×100 mL). The combined organic layers were washed with water and brine before being concentrated. The crude product was purified by column chromatography (silica gel: 60-120 mesh, petroleum ether:ethyl acetate (75:25) eluent). This yielded 4.3 g (51%) of the sub-title compound. was added After removal of DMF by distillation the reaction was quenched by the addition of water Inorganic matter was removed by filtration the aqueous layer was extracted with ethyl acetate (4×100 mL) The combined organic layers were washed with water and brine before being concentrated The crude product was purified by column chromatography (silica gel: 60-120 mesh, petroleum ether:ethyl acetate (75:25) eluent)

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

Procedure: To a solution of [2-(4-bromophenyl)ethoxy]acetic acid (14 g, 0.054 mol; see step (ii) above) in dry THF (150 mL), borane methyl sulphide (6.16 g, 0.082 mol) was added, dropwise at from 0 to 5° C. The resulting mixture was stirred at room temperature for 3 h. After cooling the reaction mixture to between 0 and 5° C., 1.5 NHCl (80 mL) was added, dropwise, and the resulting mixture was refluxed for 30 minutes. The reaction mixture was cooled to room temperature and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water and brine and concentrated to give the sub-title compound (yield: 10.8 g, 81%). After cooling the reaction mixture to between 0 and 5° C. 1.5 NHCl (80 mL) was added dropwise, and the resulting mixture was refluxed for 30 minutes The reaction mixture was cooled to room temperature extracted with ethyl acetate (2×100 mL) The combined organic layers were washed with water and brine concentrated