(R)-2-Chloro-1-(4-fluorophenyl)ethanol

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium azide (41.8 g, 642 mmol) was added to a solution consisting of (1R)-2-chloro-1-(4-fluoro-phenyl)-ethanol (37.4 g, 214 mmol) and DMF (214 mL) at rt. The reaction mixture was heated to 100° C. for 3 h, diluted with water (500 mL), and extracted with EtOAc (700 mL). The organic layer was washed with brine (500 mL), and the organic layer dried (MgSO4), filtered, and concentrated, giving the title compound as a yellow liquid, which was used without further purification (39 g, 100%). extracted with EtOAc (700 mL) The organic layer was washed with brine (500 mL) the organic layer dried (MgSO4) filtered concentrated

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

Procedure: To a solution consisting of BH3.THF (1 M, 150 mL) and (R)-(+)-2-methyl-CBS-oxazaborolidine (1 M in THF) (2.14 mL) was added a second solution consisting of 2-chloro-4′-fluoro-acetophenone (37.0 g, 214 mmol) and THF (100 ml) over 1 h at rt. The resultant colorless reaction mixture was stirred for 45 min and then quenched with MeOH (75 mL). The solvent was removed in vacuo leaving the title compound as pale yellow oil, which was used without further purification (37 g, 100%) was added a second solution quenched with MeOH (75 mL) The solvent was removed in vacuo