Pyridine → 2-(3-Bromophenoxy)isoindoline-1,3-dione

HRID 2179349Notes

Reaction equation

HRID 2179349 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[OH:11][N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22].N1C=CC=CC=1>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:11][N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10665N-HydroxyphthalimideHCID 2734318(3-Bromophenyl)boronic acid

Product 1

HCID 161203692-(3-Bromophenoxy)isoindoline-1,3-dioneYield 52.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 3-bromophenylboronic acid (246 mg, 1.23 mmol), 2-hydroxyisoindoline-1,3-dione (100 mg, 0.61 mmol), cupric acetate (223 mg, 1.23 mmol) and activated 4 Å molecular sieves (155 mg) in 1,2-dichloroethane (3 mL) under a nitrogen atmosphere was added pyridine (0.11 mL, 1.35 mmol). The reaction was stirred at ambient temperature for 24 h, concentrated in vacuo and purified by flash column chromatography (82:18 hexanes/ethyl acetate) to provide 2-(3-bromophenoxy)isoindoline-1,3-dione (102 mg, 52%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 7.93 (dd, J=5.4, 3.0 Hz, 2H), 7.83 (dd, J=5.6, 3.0 Hz, 2H), 7.33 (t, J=2.1 Hz, 1H), 7.29 (dt, J=7.8, 2.0 Hz, 1H), 7.22 (t, J=8.1, 1H), 7.16-7.10 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by flash column chromatography (82:18 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-5cc42da57a2b4b2fa089e35c3ca94878
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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