Sodium hydride → 6-Bromo-2,3-dihydro-1lambda6-benzothiophene-1,1,3-trione

HRID 2390291Notes

Reaction equation

HRID 2390291 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:3]=1.[H-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:8])[CH2:15][S:12](=[O:14])(=[O:13])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 53393139Methyl 4-bromo-2-(methylsulfonyl)benzoate2×

Product 1

HCID 565941086-Bromo-2,3-dihydro-1lambda6-benzothiophene-1,1,3-trioneYield 102.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-bromo-2-(methylsulfonyl)benzoate (Intermediate 239; 4.00 g; 13.6 mmol) in anhydrous THF (60 ml) was treated with NaH (595 mg; 13.6 mmol) and stirred at RT for 1.5 h. The reaction was quenched with water. AcOEt and a 1N solution of HCl in water were added and the phases were separated. The organic phase was washed with brine, dried on MgSO4, filtered and concentrated to give the title compound as a yellow solid (3.63 g).

Workup

  1. customThe reaction was quenched with water
  2. additionAcOEt and a 1N solution of HCl in water were added
  3. customthe phases were separated
  4. washThe organic phase was washed with brine
  5. customdried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fd212ac934024d2488fbe2f4e26a52e1
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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