Pyridine → 2-(4-Chlorophenoxy)isoindoline-1,3-dione

HRID 1697441Notes

Reaction equation

HRID 1697441 reaction equation
N1C=CC=CC=1.[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>C(Cl)Cl>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([O:7][N:8]2[C:9](=[O:18])[C:10]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]3[C:12]2=[O:13])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10665N-HydroxyphthalimideHCID 742994-Chlorophenylboronic acid

Product 1

HCID 153707352-(4-Chlorophenoxy)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.37 mL, 4.6 mmol) was added to a suspension of N-hydroxyphthalimide (664 mg, 4.1 mmol), 4-chlorophenylboronic acid (635 mg, 4.1 mmol), and powdered 4 Å molecular sieves (1.02 g) in CH2Cl2 (20 mL). Cupric acetate monohydrate (812 mg, 4.1 mmol) was added, and the mixture was stirred open to the atmosphere at room temperature for 18 hours. Silica gel (10 g) was added, and the slurry was concentrated to dryness under vacuum. The residue was applied to the top of a flash chromatography column, and eluted with hexanes:ethyl acetate (80:20) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 7.11-7.17 (m, 2 H), 7.27-7.34 (m, 2 H), 7.79-7.87 (m, 2 H), 7.88-7.95 ppm (m, 2 H).

Workup

  1. additionSilica gel (10 g) was added
  2. concentrationthe slurry was concentrated to dryness under vacuum
  3. washeluted with hexanes:ethyl acetate (80:20)

Sources & evidence

ORD record
ord-346669d5ca524b45a366a311e2e03b44
Source dataset
uspto-grants-2012_04
Patent number
US08163915B2

Reaction notes

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