2-Bromobutane → 2-(sec-butoxy)-1H-isoindole-1,3(2H)-dione

HRID 29158

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].N12CCCN=C1C[CH2:17][CH2:16][CH2:15][CH2:14]2.BrC(CC)C>CN(C=O)C>[CH:15]([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])([CH2:16][CH3:17])[CH3:14]

Participants

Conditions

Temperature: 55 °C

Procedure

N-hydroxylphthalimide (18.4 mmol, 3.0 g) was dissolved in anhydrous DMF (20 mL) under nitrogen. To the stirring solution, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (27.6 mmol, 4.13 mL) was injected followed by 2-bromobutane (22.1 mmol, 2.41 mL) and the reaction was warmed to 55° C. After stirring for 18 hour, the reaction was cooled to room temperature and concentrated to a red oil. The reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with saturated aqueous sodium bicarbonate solution, distilled water, brine and dried over magnesium sulfate. The solvent was removed under vacuum providing 3.57 g (89%) of a yellow solid. Rf: 0.8 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73 (2H,m), 4.31 (1H,m), 1.81 (1H,m), 1.64 (1H,m), 1.32 (3H,d), 1.03 (3H,t).

Workup

temperaturethe reaction was cooled to room temperature
concentrationconcentrated to a red oil
customThe reaction was partitioned between ethyl acetate and 1N HCl
washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
distillationdistilled water, brine
dry with materialdried over magnesium sulfate
customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-dfeb3f265d5d446e915bd4f1737a0a9c
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419967B2

Linked notes

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