2-(3,5-dibromophenyl)ethanol

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

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

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: In analogy to the procedure described for Building Block AW, the alkylation of 2-(3,5-dibromo-phenyl)-ethanol with iodomethane using sodium hydride as the base yielded the title compound 86% yield as a light yellow oil.

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

Procedure: A solution of (3,5-dibromo-phenyl)acetic acid (1.543 g, 5.2 mmol) in tetrahydrofuran (40 mL) was cooled to 0° C. Within 30 minutes borane tetrahydrofuran complex (1 M, 9.19 mL) was added. After complete addition the ice bath was removed and the reaction mixture warmed to room temperature within 25 minutes. After 3 hours, the mixture was cooled to −2° C., quenched by addition of methanol (10 mL) and evaporated under reduced pressure. The residue was dissolved in dichloromethane, the resulting solution was washed with hydrochloric acid (1 N, 50 mL), a saturated solution of sodium hydrogencarbonate (50 mL), and brine. The organic layer was dried over sodium sulfate and evaporated under reduced pressure and yielded. The residue was chromatographed on silica gel using a gradient of heptane/ethyl acetate=100/0 to 2/1 as the eluent. There were obtained 1.29 g (88% of theory) of the title compound as a light yellow oil. Within 30 minutes borane tetrahydrofuran complex (1 M, 9.19 mL) was added was removed the mixture was cooled to −2° C. quenched by addition of methanol (10 mL) evaporated under reduced pressure The residue was dissolved in dichloromethane the resulting solution was washed with hydrochloric acid (1 N, 50 mL) The organic layer was dried over sodium sulfate evaporated under reduced pressure yielded The residue was chromatographed on silica gel using a gradient of heptane/ethyl acetate=100/0 to 2/1 as the eluent