[5-chloro-2-(trifluoromethoxy)phenyl]methanol

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: DBU (1.0 mL, 6.7 mmol) was added to a solution of (5-chloro-2-trifluoromethoxy-phenyl)-methanol (1.2 g, 5.3 mmol) and DPPA (1.4 mL, 6.4 mmol) in toluene (30 mL) at room temperature. After 3 h, the reaction was concentrated in vacuo to yield an yellow oil. Silica gel column chromatography using 95:5 hexanes:EtOAc yielded 0.86g (65%) of 2-azidomethyl-4-chloro-1-trifluoromethoxy-benzene as a colorless oil. the reaction was concentrated in vacuo to yield an yellow oil

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

Procedure: t-Butyl nitrite (2.49 g, 24.2 mmol), copper (II) chloride (2.71 g, 20.2 mmol), and acetonitrile (100 mL) were added to a round-bottom flask. The resulting mixture was cooled to 0° C. (5-Amino-2-trifluoromethoxy-phenyl)-methanol (1.67 g, 8.1 mmol) in acetonitrile (10 mL) was slowly added to the reaction over a period of 5 min. The reaction was warmed up to room temperature and stirred overnight. The mixture was then poured into 20% HCl (100 mL) and extracted with ether (100 mL). The organic layer was washed with 20% HCl (100 mL) and dried over MgSO4. The ether was removed in vacuo and the residue was chromatographed with 4:1 hexanes:EtOAC to give 1.2 g (66%) of (5-chloro-2-trifluoromethoxy-phenyl)-methanol as a yellow solid. was slowly added to the reaction over a period of 5 min extracted with ether (100 mL) The organic layer was washed with 20% HCl (100 mL) dried over MgSO4 The ether was removed in vacuo the residue was chromatographed with 4:1 hexanes

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

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