3-[tert-butyl(dimethyl)silyl]oxy-2-fluorophenol

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3-tert-butyldimethylsilyloxy-2-fluorophenol (10.59 g, 46.8 mmol) in THF (150 ml) cooled to -70° C. was added dropwise over 5 min. sec-butyllithium (42 ml, 1.12M in cyclohexane). The reaction mixture was stirred ad -70° C. for 1 h and then poured into a slurry of dry-ice/diethyl ether. Water (200 ml) was added cautiously and the organic layer separated and discarded. The aqueous layer was acidified to pH 2 with concentrated HCl and extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried (MgSO4) and evaporated to afford title compound (7.90 g, 70%) as a white solid. the organic layer separated extracted with ethyl acetate (3×100 ml) The combined organic extracts were dried (MgSO4) evaporated

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3-tert-butyldimethylsilyloxy-2-fluorophenol (10.59 g, 46.8 mmol) in THF (150 ml) cooled to -70° C. was added dropwise over 5 min. sec-butyllithium (42 ml, 1.12M in cyclohexane). The reaction mixture was stirred ad -70° C. for 1 h and then poured into a slurry of dry-ice/diethyl ether. Water (200 ml) was added cautiously and the organic layer separated and discarded. The aqueous layer was acidified to pH 2 with concentrated HCl and extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried (MgSO4) and evaporated to afford title compound (7.90 g, 70%) as a white solid. the organic layer separated extracted with ethyl acetate (3×100 ml) The combined organic extracts were dried (MgSO4) evaporated

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

Procedure: To a solution of 2-fluorophenol (10.35 g, 9.2 mmol) and tert-butyldimethylsilyl chloride (101 mmol) in DMF (180 ml) was added imidazole (7.54 g, 110 mmol) in one portion. After stirring for 3 h the reaction mixture was poured into water (300 ml) and extracted with diethyl ether (3×100 ml). The combined extracts were washed with 10% aqueous citric acid (100 ml), brine (100 ml), dried (MgSO4) and concentrated under reduced pressure to afford title compound (20.63 g, quant.) as a colorless liquid. extracted with diethyl ether (3×100 ml) The combined extracts were washed with 10% aqueous citric acid (100 ml), brine (100 ml) dried (MgSO4) concentrated under reduced pressure