Sodium Hydroxide → 4-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoic acid

HRID 1804123Notes

Reaction equation

HRID 1804123 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][S:13]2(=[O:18])=[O:17])[CH:3]=1.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][S:13]2(=[O:17])=[O:18])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58484624Methyl 4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoate

Product 1

HCID 549330084-Bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To methyl 4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoate (5.57 g) described in Preparation Example 116 were added ethanol (43 mL) and 1N aqueous sodium hydroxide solution (21.7 mL) and the mixture was stirred at 60° C. for 40 min. Ethanol was evaporated and the mixture was neutralized with water and 1N hydrochloric acid under ice-cooling and the mixture was stirred. The precipitated crystal were collected by filtration to give the title compound (5.25 g).

Workup

  1. customEthanol was evaporated
  2. temperaturecooling
  3. stirringthe mixture was stirred
  4. filtrationThe precipitated crystal were collected by filtration

Sources & evidence

ORD record
ord-9e7de342340d441ca09e6caac18c3265
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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