Water → 2-[4,4-Bis-(4-fluoro-phenyl)-butyl]-isoindole-1,3-dione

HRID 990325Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[K].O>CN(C=O)C>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:4][CH2:3][CH2:2][N:24]2[C:20](=[O:30])[C:21]3[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:23]2=[O:25])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension consisting of 1,1′-(4-bromobutylidene)bis[4-fluorobenzene] (25 g, 77 mmol) and potassium phthalimide (17 g, 92 mmol) in 300 mL DMF was stirred at 50° C. for 16 hours, cooled to 25° C., and poured into 900 mL of cold H2O. The mixture was extracted with ethyl acetate (3×300 mL), and the combined extracts were washed with H2O (2×1 L), followed by brine (700 mL), then dried over anhydrous sodium sulfate. Evaporation of solvent in vacuo afforded 28.6 g of a golden oil, which was triturated with 250 mL 2,2,4-trimethylpentane containing 5% 2-propanol, and the solid thus obtained was collected by filtration and dried at 50° C. in vacuo, to give 28.7 g (97%) of titled compound as a white powder; mp 69-70° C. APCI-MS m/z 391.1 (M−).

Workup

temperaturecooled to 25° C.
extractionThe mixture was extracted with ethyl acetate (3×300 mL)
washthe combined extracts were washed with H2O (2×1 L)
dry with materialdried over anhydrous sodium sulfate
customEvaporation of solvent in vacuo

Sources & evidence

ORD record: ord-db8b8e497ccc49cbb4fa63cf44701a66
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06458781B1

Reaction notes

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