4-Bromomethyl-2-phenylthiophene → 2-(5-Phenylthiophen-3-ylmethyl)isoindole-1,3-dione

HRID 915695Notes

Reaction equation

HRID 915695 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15]1[CH:16]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:18][CH:19]=1>CN(C)C=O>[C:20]1([C:17]2[S:18][CH:19]=[C:15]([CH2:14][N:5]3[C:1](=[O:11])[C:2]4[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4]3=[O:6])[CH:16]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 198410854-Bromomethyl-2-phenylthiopheneHCID 24194345Phthalimide potassium salt

Product 1

HCID 691299712-(5-Phenylthiophen-3-ylmethyl)isoindole-1,3-dioneYield 85.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Prepare a solution of potassium phthalimide (457 mg, 2.47 mmol) in dimethylformamide (6 mL). Add a solution of 4-bromomethyl-2-phenyl-thiophene (523 mg, 2.06 mmol) in dimethylformamide (6 mL), dropwise. Stir the reaction mixture overnight at room temperature under nitrogen. Concentrate the solution, redissolve in ethyl acetate, wash with saturated aqueous sodium hydrogencarbonate (20 mL), then brine (20 mL). Dry (magnesium sulfate), filter aid concentrate. Preform flash chromatography of the resulting residue on silica gel eluting with 5:1 hexane/ethyl acetate to afford 565 mg of 2-(5-phenylthiophen-3-ylmethyl)isoindole-1,3-dione as a yellow solid. 1H NMR (CDCl3) δ 7.84-7.88 (m, 2H), 7.70-7.72 (m, 2H0, 7.54-7.57 (m, 2H), 7.25-7.34 (m, 5H), 4.83 (s, 2H).

Workup

  1. concentrationConcentrate the solution
  2. dissolutionredissolve in ethyl acetate
  3. washwash with saturated aqueous sodium hydrogencarbonate (20 mL)
  4. dry with materialDry (magnesium sulfate)
  5. filtrationfilter aid
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-dd9e7a2eee5248b099fc64796f3aca11
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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