Sodium Hydroxide → 5-Bromo-3-hydroxyisoindolin-1-one

HRID 1503537Notes

Reaction equation

HRID 1503537 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7]2=[O:14]>[Zn].O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH:7]2[OH:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2360184-Bromophthalimide

Product 1

HCID 116155375-Bromo-3-hydroxyisoindolin-1-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 24463Copper sulfate pentahydrateCatalyst

Conditions

Temperature
0 °C

Procedure

A mixture of Zn powder (1.73 g, 26.154 mmol), copper (II) sulfate pentahydrate (0.02 g, 0.08 mmol) and 2M aq NaOH (27 mL) were cooled to 0° C. 5-Bromoisoindoline-1,3-dione (5 g, 22 mmol) was added at the same temperature over the period of 30 min. The reaction mixture was stirred at 0° C. for 30 min and 3 h at RT. The reaction mixture was filtered and the filtrate was neutralized with concentrated HCl. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude title compound as a brown solid, which was used in the next step without further purification (1.3 g): mp 258-261° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.03 (br, 1H), 7.81 (m, 2H), 7.69 (m, 1H), 6.44 (m, 1H), 5.88 (d, J=9.3 Hz, 1H); ESIMS m/z 225.83 ([M−H]−); IR (thin film) 1684, 3246, 606 cm−1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionThe reaction mixture was diluted with ethanol
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-af606ca80c324852bf893451dad2b5cd
Source dataset
uspto-grants-2015_12
Patent number
US09212163B2

Reaction notes

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