Sodium Iodide → 1-[2-(4-Fluoro-phenyl)-ethyl]-pyrrolidine-2,5-dione

HRID 853705Notes

Reaction equation

Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[NH:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[F:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][N:11]2[C:15](=[O:16])[CH2:14][CH2:13][C:12]2=[O:17])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(2-bromo-ethyl)-4-fluoro-benzene (587 mg, 3.7 mmol) and pyrrolidine-2,5-dione (succinimide, 733.3 mg, 7.4 mmol) in dimethylformamide (15 ml) was added potassium carbonate (2.0 g, 14.8 mmol) and sodium iodide (277 mg, 1.9 mmol). The reaction mixture was warmed to 60° C. and kept at 60° C. overnight with stirring. The reaction mixture was cooled to room temperature and concentrated in vacuo. The concentrate was diluted with ethyl acetate and washed twice with a saturated sodium bicarbonate aqueous solution, twice with water, once with brine, and concentrated in vacuo. The residue was purified by silica gel chromatography (100% ethylacetate) to afford 1-[2-(4-fluoro-phenyl)-ethyl]-pyrrolidine-2,5-dione 309 (570 mg, 2.6 mmol, 70%) as a solid. 1H NMR (CDCl3) δ 7.14 (m, 2H), 6.94 (t, 2H), 3.68 (t, 2H), 2.84 (t, 2H), 2.63 (s, 4H).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
additionThe concentrate was diluted with ethyl acetate
washwashed twice with a saturated sodium bicarbonate aqueous solution, twice with water, once with brine
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (100% ethylacetate)

Sources & evidence

ORD record: ord-e738e0c7f58841abbd456f71309b1dad
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253180B2

Reaction notes

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