Chloroacetic Acid → 7041-52-3

HRID 1085351Notes

Reaction equation

HRID 1085351 reaction equation
[S:1]([O-:4])([O-])=[O:2].[Na+].[Na+].[C:7](=O)(O)[O-].[Na+].BrC1C=C(S(Cl)(=O)=O)C=CC=1C(Cl)=O.ClCC(O)=O.[OH-].[Na+].[Br:33][C:34]1[CH2:42][C:41](=S=O)[CH:40]=[CH:39][C:35]=1[C:36]([OH:38])=[O:37].Cl>O>[Br:33][C:34]1[CH:42]=[C:41]([S:1]([CH3:7])(=[O:4])=[O:2])[CH:40]=[CH:39][C:35]=1[C:36]([OH:38])=[O:37]

Participants

9

Reactant 7

HCID 300Chloroacetic Acid2×HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 19814735HCID 19814735, compoundHCID 86744728HCID 86744728, compound

Product 1

HCID 142570057041-52-3Yield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A 50 mL round bottom flask equipped with a reflux condenser, thermometer and magnetic stirrer was charged with 1.6 g (13 mmol) of sodium sulfite, 4.2 g (50 mmol) of sodium bicarbonate and 20 mL of water. The resulting slurry was heated to 75° C. and 4.0 g (13 mmol) of 2-bromo-4-(chlorosulfonyl)benzoyl chloride was added over 30 minutes. After heating at 75° C. for one hour, chloroacetic acid (1.8 g, 19 mmol) and 1.0 mL (19 mmol) of 50% aqueous sodium hydroxide were added sequentially to the aqueous solution of 2-bromo-4-sulfinylbenzoic acid, and the reaction mixture heated to reflux. Additional chloroacetic acid (2.0 g) was added as necessary to drive the reaction to completion. After heating for 16 hours, the reaction mixture was allowed to cool to ambient temperature and acidified with concentrated HCl. The precipitated solids were collected by filtration and dried to give 1.6 g of 2-bromo-4-(methylsulfonyl)benzoic acid, corresponding to a 46% yield.

Workup

  1. customA 50 mL round bottom flask equipped with a reflux condenser
  2. temperatureAfter heating at 75° C. for one hour
  3. temperaturethe reaction mixture heated to reflux
  4. customthe reaction to completion
  5. temperatureAfter heating for 16 hours
  6. temperatureto cool to ambient temperature
  7. filtrationThe precipitated solids were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-fb3e3da0ce474d0ba8b05f3ec271554b
Source dataset
uspto-grants-1991_04
Patent number
US05008448

Reaction notes

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