methyl 3-(tert-butoxycarbonylamino)-2-fluorobenzoate

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

Procedure: A solution of monomethyl 2-fluoroisophthalate (0.4 g) in tert-butyl alcohol (10 mL) was treated with Et3N (0.56 mL) and diphenylphosphoryl azide (0.75 mL). After 1 h, the mixture was heated at reflux for 24 h, then cooled and concentrated. The residue was diluted with EtOAc, washed with saturated aqueous NaHCO3, dried over MgSO4, filtered, and evaporated. Silica gel chromatography (acetone/hexane gradient) provided the product. 1H-NMR (CDCl3): δ 8.31 (1H, br t, J=7.2 Hz), 7.55 (1H, ddd, J=1.6, 6.8, 8.0 Hz), 7.16 (1H, ddd, J=1.2, 8.0, 8.0 Hz), 6.80 (1H, br s), 3.93 (3H, s), 1.54 (9H, s). the mixture was heated at reflux for 24 h cooled concentrated The residue was diluted with EtOAc washed with saturated aqueous NaHCO3 dried over MgSO4 filtered evaporated Silica gel chromatography (acetone/hexane gradient) provided the product

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

Procedure: A solution of monomethyl 2-fluoroisophthalate (0.4 g) in tert-butyl alcohol (10 mL) was treated with Et3N (0.56 mL) and diphenylphosphoryl azide (0.75 mL). After 1 h, the mixture was heated at reflux for 24 h, then cooled and concentrated. The residue was diluted with EtOAc, washed with saturated aqueous NaHCO3, dried over MgSO4, filtered, and evaporated. Silica gel chromatography (acetone/hexane gradient) provided the product. 1H-NMR (CDCl3): δ 8.31 (1H, br t, J=7.2 Hz), 7.55 (1H, ddd, J=1.6, 6.8, 8.0 Hz), 7.16 (1H, ddd, J=1.2, 8.0, 8.0 Hz), 6.80 (1H, br s), 3.93 (3H, s), 1.54 (9H, s). the mixture was heated at reflux for 24 h cooled concentrated The residue was diluted with EtOAc washed with saturated aqueous NaHCO3 dried over MgSO4 filtered evaporated Silica gel chromatography (acetone/hexane gradient) provided the product

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

Procedure: A solution of monomethyl 2-fluoroisophthalate (0.4 g) in tert-butyl alcohol (10 mL) was treated with Et3N (0.56 mL) and diphenylphosphoryl azide (0.75 mL). After 1 h, the mixture was heated at reflux for 24 h, then cooled and concentrated. The residue was diluted with EtOAc, washed with saturated aqueous NaHCO3, dried over MgSO4, filtered, and evaporated. Silica gel chromatography (acetone/hexane gradient) provided the product. 1H-NMR (CDCl3): δ 8.31 (1H, br t, J=7.2 Hz), 7.55 (1H, ddd, J=1.6, 6.8, 8.0 Hz), 7.16 (1H, ddd, J=1.2, 8.0, 8.0 Hz), 6.80 (1H, br s), 3.93 (3H, s), 1.54 (9H, s). the mixture was heated at reflux for 24 h cooled concentrated The residue was diluted with EtOAc washed with saturated aqueous NaHCO3 dried over MgSO4 filtered evaporated Silica gel chromatography (acetone/hexane gradient) provided the product