Pyridine → N-phenoxyphthalimide

HRID 922295Notes

Reaction equation

HRID 922295 reaction equation
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCCl.C(Cl)Cl.[Cu]Cl>[O:1]([N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 10665N-HydroxyphthalimideHCID 66827Phenylboronic Acid

Product 1

HCID 3560555N-phenoxyphthalimide

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a 50 mL single neck RB flask wash charged with 2-hydroxy-1H-isoindole-1,3(2H)-dione (1 g, 6.13 mmol), 4 A° molecular sieves (1 g) and copper (I) chloride (0.61 g, 0.06 mmol) in DCE under open atmosphere. To the stirred reaction mixture, was added phenyl boronic acid (1.5 g, 12.2 mmol) followed by pyridine (0.53 g, 6.7 mmol) drop wise. Resulting mixture was stirred at RT for 12 h. The Reaction mixture was diluted with DCM and then filtered through celite pad. The organic layer was washed with saturated brine solution (50 mL) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford off white solid. 1H NMR (300 MHz, CDCl3): δ 7.83-7.86 (q, 2H), 7.73-7.77 (m, 2H), 7.28-7.30 (m, 2H), 7.07-7.11 (m, 3H).

Workup

  1. washTo a 50 mL single neck RB flask wash
  2. customTo the stirred reaction mixture
  3. customResulting mixture
  4. filtrationfiltered through celite pad
  5. washThe organic layer was washed with saturated brine solution (50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customto afford off white solid

Sources & evidence

ORD record
ord-caecc14e1b934f14b308a5505de5c900
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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