Phthalimide → 2-[1-(4-Bromo-phenyl)-ethyl]-isoindole-1,3-dione

HRID 1028462Notes

Reaction equation

HRID 1028462 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6](O)[CH3:7])=[CH:4][CH:3]=1.[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([N:15]2[C:11](=[O:21])[C:12]3[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14]2=[O:16])[CH3:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 953521-(4-Bromophenyl)ethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 607032812-[1-(4-Bromo-phenyl)-ethyl]-isoindole-1,3-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-α-methylbenzylalcohol (3.0 g, 0.015 mol), phthalimide (2.2 g, 0.015 mol) and triphenylphosphine (6.0 g, 0.023 mol) in tetrahydrofuran was added diethyl azodicarboxylate (4.0 g, 0.023 mol) and the reaction mixture was stirred at room temperature for 14 hours. The solution was concentrated and the crude material was purified on silica gel (10˜35% ethyl acetate in hexane) to give 2.93 g of the title compound (60% yield) 1H NMR (300 MHz, CDCl3) δ ppm 1.90 (d, J=7.35 Hz, 3 H) 5.52 (q, J=7.11 Hz, 1 H) 7.34-7.41 (m, 2 H) 7.41-7.50 (m, 2 H) 7.65-7.74 (m, 2 H) 7.76-7.86 (m, 2 H) MS (ESI), m/z 404.0 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. customthe crude material was purified on silica gel (10˜35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bffd073c38a2490280f8d075b1a0ce96
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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