1-Bromo-2-(chloromethyl)-4,5-dimethoxybenzene → 2-(2-Bromo-4,5-dimethoxy-benzyl)isoindole-1,3-dione

HRID 1186031Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12]Cl.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][N:18]1[C:14](=[O:24])[C:15]2[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17]1=[O:19]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 1-bromo-2-chloromethyl-4,5-dimethoxy-benzene (26.01 g, 0.09796 mol) in dry DMF (100 mL) was treated with potassium phthalimide (19.05 g, 0.1029 mol). The resulting slurry was heated to 80° C. while stirring under nitrogen for 4.5 h. The resulting mixture was then cooled to room temperature and allowed to stir 16 h. The resulting mixture solidified, was diluted with water (400 mL) and stirred 1 h. The resulting white precipitate was collected via filtration and washed with water (1 L). The white solid was dissolved in boiling methanol (2 L). The resulting solution was reduced to about 1 L, at which time a precipitate began to form. The resulting slurry was allowed to cool to room temperature then placed on an ice bath. The precipitate was collected via filtration to yield 2-(2-bromo-4,5-dimethoxy-benzyl)-isoindole-1,3-dione as a white solid.

Workup

temperatureThe resulting mixture was then cooled to room temperature
stirringto stir 16 h
stirringstirred 1 h
filtrationThe resulting white precipitate was collected via filtration
washwashed with water (1 L)
dissolutionThe white solid was dissolved
customto form
temperatureto cool to room temperature
customthen placed on an ice bath
filtrationThe precipitate was collected via filtration

Sources & evidence

ORD record: ord-bfff45a4ef294fe28467f0b43f6d481b
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673890B2

Reaction notes

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