5-Chloro-1-(3H)-Isobenzofuranone

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: Methylamine gas was condensed into a sealed tube at −78° C., and a solution of 5-chloro-2-benzofuran-1(3H)-one (6.68 g, 39.8 mmol) in methanol (30 mL) was added. The solution was slowly warmed to room temperature overnight; The reaction was concentrated in vacuo, and the residue was partitioned between water and and chloroform. After three extractions with chloroform, the combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 4-chloro-2-(hydroxymethyl)-N-methylbenzamide. condensed into a sealed tube at −78° C. The reaction was concentrated in vacuo the residue was partitioned between water and and chloroform After three extractions with chloroform the combined organics were dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: Methylamine gas was condensed into a sealed tube at −78° C., and a solution of 5-chloro-2-benzofuran-1(3H)-one (6.68 g, 39.8 mmol) in methanol (30 mL) was added. The solution was slowly warmed to room temperature overnight; The reaction was concentrated in vacuo, and the residue was partitioned between water and and chloroform. After three extractions with chloroform, the combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 4-chloro-2-(hydroxymethyl)-N-methylbenzamide. condensed into a sealed tube at −78° C. The reaction was concentrated in vacuo the residue was partitioned between water and and chloroform After three extractions with chloroform the combined organics were dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: To a solution of 5-chlorophthalide (3.64 g, 21.6 mmol) in dichloromethane (100 mL) at −78° C. was added di-isobutylaluminium hydride (1M in toluene) (23.8 mL, 23.8 mmol) dropwise. After 1 h the reaction mixture was quenched with a saturated solution of sodium tartrate (250 mL), allowed to warm to room temperature and stirred for 1 h. The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to yield the title compound as a white solid. After 1 h the reaction mixture was quenched with a saturated solution of sodium tartrate (250 mL) The layers were separated the aqueous layer extracted with dichloromethane The combined organic layers were dried (MgSO4) filtered concentrated in vacuo