(5-iodo-2-methylphenyl)methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of ester 4 (41.0 g, 141 mmol) in THF (300 mL) was added lithium borohydride (2.0 M in THF, 212 mL). The reaction mixture was refluxed overnight. After cooling to 0° C., the reaction was quenched by addition of aq. saturated NH4Cl solution. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to yield the titled compound (34.0 g, 97%) as a white solid, which was carried on to the next step without further purification. The reaction mixture was refluxed overnight the reaction was quenched by addition of aq. saturated NH4Cl solution The mixture was diluted with water extracted with EtOAc The organic layer was washed with brine dried over anhydrous MgSO4 filtered evaporated in vacuo