Hydrochloric Acid → HCID 56594115, compound

HRID 2390302Notes

Reaction equation

HRID 2390302 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:3]=1.[OH-].[Na+].Cl>C1COCC1.O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 56594110HCID 56594110, compound2×

Product 1

HCID 56594115HCID 56594115, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 4-bromo-2-(isopropylsulfonyl)benzoate (Intermediate 242; 516 mg; 1.61 mmol) in THF (10 ml) was treated with a 5 N solution of NaOH in water (4 mL) and the reaction mixture was heated at 60° C. for 1 day. The reaction mixture was acidified with aqueous HCl and the reaction mixture was extracted 3 times with EtOAc. The combined organic phases were dried over MgSO4, filtered and concentrated to dryness affording the title compound as a pale yellow solid (386 mg; 78%).

Workup

  1. extractionthe reaction mixture was extracted 3 times with EtOAc
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1f1304549e074cb883daab9e5d422879
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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