Chloroacetic Acid → (4-Bromo-phenylsulfanyl)-acetic acid

HRID 2390956Notes

Reaction equation

HRID 2390956 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.Cl[CH2:12][C:13]([OH:15])=[O:14].Cl>C1(C)C=CC=CC=1.O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 660494-Bromothiophenol

Product 1

HCID 55676(4-Bromo-phenylsulfanyl)-acetic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To water (600 mL) solution of 88.9 g of sodium hydroxide was added 200 g of 4-bromothiophenol and dropwise added water (300 mL) solution of 105 g of chloroacetic acid, which was then stirred at 60 to 70° C. for 1 hour. After cooling the reaction mixture to 40° C., thereto were added 140 mL of hydrochloric acid and 600 mL of toluene, which was then heated to 80° C. The organic layer was separated and slowly cooled to 5° C. After stirring at the same temperature for 1 hour, the crystals precipitate was collected by filtration to provide 243 g of (4-bromophenylthio)acetic acid as white solid form.

Workup

  1. temperatureAfter cooling the reaction mixture to 40° C.
  2. temperaturewas then heated to 80° C
  3. customThe organic layer was separated
  4. temperatureslowly cooled to 5° C
  5. stirringAfter stirring at the same temperature for 1 hour
  6. filtrationthe crystals precipitate was collected by filtration

Sources & evidence

ORD record
ord-ea68e09636cd4c0ab7b4faadd7696c26
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

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