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

HRID 1406284Notes

Reaction equation

HRID 1406284 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+].O>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

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 53393139Methyl 4-bromo-2-(methylsulfonyl)benzoate

Product 1

HCID 565941086-Bromo-2,3-dihydro-1lambda6-benzothiophene-1,1,3-trioneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-bromo-2-(methylsulfonyl)benzoate (774 mg, 2.64 mmol) in anhydrous THF (10 mL) was added NaH (60% in mineral, 111 mg, 2.77 mmol). The mixture was stirred at room temperature for 5 hr. The reaction was monitored by LCMS for completion. H2O (1 mL) was added to quench the reaction followed by the addition of aqueous hydrochloric acid (1N, 50 mL) and EtOAc (50 mL). The organic layer was separated, and the water layer was extracted with 2×EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (689 mg, 100%) as a white solid.

Workup

  1. customto quench the reaction
  2. additionfollowed by the addition of aqueous hydrochloric acid (1N, 50 mL) and EtOAc (50 mL)
  3. customThe organic layer was separated
  4. extractionthe water layer was extracted with 2×EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-42100e23bf474aedb73893928793a97c
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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