(5-amino-2-chloro-4-fluorophenyl)methanol

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

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

Procedure: A mixture of 4.9 g (0.028 mole) of 2-chloro-4-fluoro-5-aminobenzyl alcohol, 4.25 g (0.028 mole) of tetrahydrophthalic anhydride, and 100 ml of tetrahydrofuran was refluxed overnight. The solvent was evaporated under reduced pressure, leaving a thick, black oil. To this residue was added 100 ml of acetic acid, and the mixture was heated at 100° C. for several hours. The solvent was evaporated under reduced pressure and was replaced with 200 ml of ethyl acetate. This solution was washed three times with 150 ml of a saturated, aqueous solution of sodium bicarbonate and three times with 150 ml of 10% hydrochloric acid. The solution was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure, leaving 8.80 g of a viscous, black oil. This oil was passed through a column of silica gel, eluting with ethyl acetate/heptane (7/13). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure, yielding 6.3 g of N-[4-chloro-2-fluoro- 5-(methylcarbonyloxymethyl)phenyl]-3,4,5,6-tetrahydrophthalimide as a thick, amber oil. The nmr and ir spectra were consistent with the proposed structure. was refluxed overnight The solvent was evaporated under reduced pressure leaving a thick, black oil The solvent was evaporated under reduced pressure This solution was washed three times with 150 ml of a saturated, aqueous solution of sodium bicarbonate and three times with 150 ml of 10% hydrochloric acid The solution was dried over anhydrous magnesium sulfate filtered the solvent was evaporated under reduced pressure leaving 8.80 g of a viscous, black oil eluting with ethyl acetate/heptane (7/13) the solvent was evaporated under reduced pressure

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

Procedure: In a Parr hydrogenation apparatus were placed 6.5 g (0.032 mole) of 2-chloro-4-fluoro-5-nitrobenzyl alcohol, 0.3 g of platinum oxide catalyst, and 100 ml of glacial acetic acid. Hydrogenation required 1.5 hours after which the catalyst was removed by filtration and the solvent was evaporated under reduced pressure, leaving 5.42 g of 2-chloro-4-fluoro-5-aminobenzyl alcohol as a tan solid. The nmr and ir spectra were consistent with the proposed structure. Hydrogenation required 1.5 hours after which the catalyst was removed by filtration the solvent was evaporated under reduced pressure

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

Procedure: A mixture of 4.9 g (0.028 mole) of 2-chloro-4-fluoro-5-aminobenzyl alcohol, 4.25 g (0.028 mole) of tetrahydrophthalic anhydride, and 100 ml of tetrahydrofuran was refluxed overnight. The solvent was evaporated under reduced pressure, leaving a thick, black oil. To this residue was added 100 ml of acetic acid, and the mixture was heated at 100° C. for several hours. The solvent was evaporated under reduced pressure and was replaced with 200 ml of ethyl acetate. This solution was washed three times with 150 ml of a saturated, aqueous solution of sodium bicarbonate and three times with 150 ml of 10% hydrochloric acid. The solution was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure, leaving 8.80 g of a viscous, black oil. This oil was passed through a column of silica gel, eluting with ethyl acetate/heptane (7/13). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure, yielding 6.3 g of N-[4-chloro-2-fluoro- 5-(methylcarbonyloxymethyl)phenyl]-3,4,5,6-tetrahydrophthalimide as a thick, amber oil. The nmr and ir spectra were consistent with the proposed structure. was refluxed overnight The solvent was evaporated under reduced pressure leaving a thick, black oil The solvent was evaporated under reduced pressure This solution was washed three times with 150 ml of a saturated, aqueous solution of sodium bicarbonate and three times with 150 ml of 10% hydrochloric acid The solution was dried over anhydrous magnesium sulfate filtered the solvent was evaporated under reduced pressure leaving 8.80 g of a viscous, black oil eluting with ethyl acetate/heptane (7/13) the solvent was evaporated under reduced pressure

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

Procedure: In a Parr hydrogenation apparatus were placed 6.5 g (0.032 mole) of 2-chloro-4-fluoro-5-nitrobenzyl alcohol, 0.3 g of platinum oxide catalyst, and 100 ml of glacial acetic acid. Hydrogenation required 1.5 hours after which the catalyst was removed by filtration and the solvent was evaporated under reduced pressure, leaving 5.42 g of 2-chloro-4-fluoro-5-aminobenzyl alcohol as a tan solid. The nmr and ir spectra were consistent with the proposed structure. Hydrogenation required 1.5 hours after which the catalyst was removed by filtration the solvent was evaporated under reduced pressure

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

Procedure: A mixture of 4.9 g (0.028 mole) of 2-chloro-4-fluoro-5-aminobenzyl alcohol, 4.25 g (0.028 mole) of tetrahydrophthalic anhydride, and 100 ml of tetrahydrofuran was refluxed overnight. The solvent was evaporated under reduced pressure, leaving a thick, black oil. To this residue was added 100 ml of acetic acid, and the mixture was heated at 100° C. for several hours. The solvent was evaporated under reduced pressure and was replaced with 200 ml of ethyl acetate. This solution was washed three times with 150 ml of a saturated, aqueous solution of sodium bicarbonate and three times with 150 ml of 10% hydrochloric acid. The solution was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure, leaving 8.80 g of a viscous, black oil. This oil was passed through a column of silica gel, eluting with ethyl acetate/heptane (7/13). The appropriate fractions were combined, and the solvent was evaporated under reduced pressure, yielding 6.3 g of N-[4-chloro-2-fluoro- 5-(methylcarbonyloxymethyl)phenyl]-3,4,5,6-tetrahydrophthalimide as a thick, amber oil. The nmr and ir spectra were consistent with the proposed structure. was refluxed overnight The solvent was evaporated under reduced pressure leaving a thick, black oil The solvent was evaporated under reduced pressure This solution was washed three times with 150 ml of a saturated, aqueous solution of sodium bicarbonate and three times with 150 ml of 10% hydrochloric acid The solution was dried over anhydrous magnesium sulfate filtered the solvent was evaporated under reduced pressure leaving 8.80 g of a viscous, black oil eluting with ethyl acetate/heptane (7/13) the solvent was evaporated under reduced pressure

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

Procedure: In a Parr hydrogenation apparatus were placed 6.5 g (0.032 mole) of 2-chloro-4-fluoro-5-nitrobenzyl alcohol, 0.3 g of platinum oxide catalyst, and 100 ml of glacial acetic acid. Hydrogenation required 1.5 hours after which the catalyst was removed by filtration and the solvent was evaporated under reduced pressure, leaving 5.42 g of 2-chloro-4-fluoro-5-aminobenzyl alcohol as a tan solid. The nmr and ir spectra were consistent with the proposed structure. Hydrogenation required 1.5 hours after which the catalyst was removed by filtration the solvent was evaporated under reduced pressure