5-bromo-1-methyl-2,3-dihydro-1H-isoindole

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: 67.46 g of 5-bromo-1-methyl-2-(p-toluene sulfonyl)isoindoline (3-8) was suspended in 325 ml of 47% hydrobromic acid and 48 ml of phenol and 197 ml of propionic acid were added thereto and the resulting mixture was heated under reflux for 4 hours. After the reaction was completed, the reaction mixture was adjusted to be alkaline with 8N sodium hydride solution and extracted with chloroform and the resulting organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel chromatopraphy (eluent; chloroform:methanol=19:1) to obtain 35.03 g of 5-bromo-1-methylisoindoline. the resulting mixture was heated under reflux for 4 hours extracted with chloroform the resulting organic layer was dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the resulting residue was purified by silica gel chromatopraphy (eluent; chloroform:methanol=19:1)

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

Procedure: 67.46 g of 5-bromo-1-methyl-2-(p-toluene sulfonyl)isoindoline (3-8) was suspended in 325 ml of 47% hydrobromic acid and 48 ml of phenol and 197 ml of propionic acid were added thereto and the resulting mixture was heated under reflux for 4 hours. After the reaction was completed, the reaction mixture was adjusted to be alkaline with 8N sodium hydride solution and extracted with chloroform and the resulting organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel chromatopraphy (eluent; chloroform:methanol=19:1) to obtain 35.03 g of 5-bromo-1-methylisoindoline. the resulting mixture was heated under reflux for 4 hours extracted with chloroform the resulting organic layer was dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the resulting residue was purified by silica gel chromatopraphy (eluent; chloroform:methanol=19:1)

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

Procedure: 67.46 g of 5-bromo-1-methyl-2-(p-toluene sulfonyl)isoindoline (3-8) was suspended in 325 ml of 47% hydrobromic acid and 48 ml of phenol and 197 ml of propionic acid were added thereto and the resulting mixture was heated under reflux for 4 hours. After the reaction was completed, the reaction mixture was adjusted to be alkaline with 8N sodium hydride solution and extracted with chloroform and the resulting organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel chromatopraphy (eluent; chloroform:methanol=19:1) to obtain 35.03 g of 5-bromo-1-methylisoindoline. the resulting mixture was heated under reflux for 4 hours extracted with chloroform the resulting organic layer was dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the resulting residue was purified by silica gel chromatopraphy (eluent; chloroform:methanol=19:1)