Water → HCID 67469414, compound

HRID 928905Notes

Reaction equation

[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[Br:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18]Br.C(N(CC)CC)C.O>CN(C=O)C>[Br:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of N-hydroxyphthalimide (352 mg, 2.16 mmol) in 4 mL of DMF was added 2-bromoethyl ether (500 mg, 2.16 mmol) followed by triethylamine (218 mg, 2.16 mmol), and the resulting solution was stirred at 45° C. overnight. Water was added to quench the reaction, the aqueous layer was extracted with ethyl acetate for 3 times, the combined organic layers were washed with brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure, the crude product was purified by silica gel column chromatography (hexanes: ethyl acetate 2:1) to afford 2-(2-(2-bromoethoxy)ethoxy)isoindoline-1,3-dione (550 mg, 1.75 mmol, 81%) as colorless oil. 1H NMR (CDCl3, 500 MHz) δ (ppm): 3.38 (t, J=6.2 Hz, 2H), 3.81 (t, J=6.2 Hz, 2H), 3.87 (t, J=4.1 Hz, 2H), 4.37 (t, J=4.1 Hz, 2H), 7.73 (dd, J=3.0, 5.0 Hz, 2H), 7.82 (dd, J=3.2, 5.0 Hz, 2H).

Workup

customto quench
customthe reaction
extractionthe aqueous layer was extracted with ethyl acetate for 3 times
washthe combined organic layers were washed with brine
dry with materialdried over anhydrous Na2SO4
customSolvent was removed under reduced pressure
customthe crude product was purified by silica gel column chromatography (hexanes: ethyl acetate 2:1)

Sources & evidence

ORD record: ord-a6578ab87b4c43c9a5008259ddc166ee
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290791B2

Reaction notes

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