Water → 2-(1-Methylethoxy)-1H-isoindole-1,3(2H)-dione

HRID 600951Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].[CH:19](Br)([CH3:21])[CH3:20].O>CS(C)=O>[CH:19]([O:7][N:8]1[C:9](=[O:18])[C:10]2[C:11](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:13])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 25 °C

Procedure

Solid potassium carbonate (8.64 g, 62.5 mmol) was added to a solution of N-hydroxyphthalimide (4.08 g, 25.0 mmol) in dimethyl sulfoxide (37 mL), and the mixture was stirred at 25° C. for 5 min. To the mixture, isopropyl bromide (3.41 mL, 37.5 mmol) was added, and the mixture stirred at 80° C. for 3 h. After ice-cooling, the mixture was poured into cold water and the resulting precipitate was collected by filtration in vacuo, washed with water (25 mL) and hexanes (15 mL) and dried in vacuo to afford 2-isopropyloxy-isoindole-1,3-dione (4.44 g, 86.6%) as a white solid which was used in the next step without further purification.

Workup

stirringthe mixture stirred at 80° C. for 3 h
temperatureAfter ice-cooling
filtrationthe resulting precipitate was collected by filtration in vacuo
washwashed with water (25 mL) and hexanes (15 mL)
customdried in vacuo

Sources & evidence

ORD record: ord-1a14b19a546e44f4939490745ee5b5fc
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902248B2

Reaction notes

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