Potassium Hydroxide → 5-bromo-3-hydroxy-3H-isobenzofuran-1-one

HRID 389937Notes

Reaction equation

HRID 389937 reaction equation
Br[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Br:11])[CH:9]=2)[C:4](=[O:12])[O:3]1.[OH-].[K+].S(=O)(=O)(O)[O-:16].[K+]>O>[Br:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4](=[O:12])[O:3][CH:2]2[OH:16]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 516920Potassium bisulfateHCID 577917913,5-dibromoisobenzofuran-1(3H)-one

Product 1

HCID 142348425-bromo-3-hydroxy-3H-isobenzofuran-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of EXAMPLE 1A (5 g, 17.1 mmol) in water (40 mL) was added powdered potassium hydroxide (1.92 g, 34.3 mmol), and the mixture was refluxed for 1 hour. After cooling, potassium bisulfate (2 g) was added, and the mixture extracted with ethyl acetate (150 mL). The organics were concentrated on a rotary evaporator and dried under vacuum to yield the title compound. MS (ESI) m/z 230 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. extractionthe mixture extracted with ethyl acetate (150 mL)
  4. concentrationThe organics were concentrated on a rotary evaporator
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1ef850ba18a041cbaa28e8e963f68c10
Source dataset
uspto-grants-2013_02
Patent number
US08383623B2

Reaction notes

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