N-Iodosuccinimide → HCID 58385810, compound

HRID 1038344Notes

Reaction equation

HRID 1038344 reaction equation
[I:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>S(=O)(=O)(O)O>[Br:9][C:10]1[CH:18]=[C:17]([CH3:19])[C:16]([I:1])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 2262922-Bromo-4-methylbenzoic acid

Product 1

HCID 58385810HCID 58385810, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
7.5 °C

Procedure

N-Iodosuccinimide (19.1 g) is added in portions to an ice-cold solution of 2-bromo-4-methyl-benzoic acid (18.4 g) dissolved in sulphuric acid (20 mL). The resulting mixture is stirred at 5-10° C. for 3 h before warming to room temperature overnight. Then, the mixture is poured on crushed ice and the resultant solution is extracted with ethyl acetate. The combined extracts are washed in succession with aqueous 10% Na2S2O3 solution (2×), water (3×), and brine (1×). After drying (MgSO4), the organic solvent is evaporated under reduced. The remaining solid is taken up in water and the resulting slurry is stirred at 70° C. for 5 min. The non-dissolving part is separated by filtration and dried to give the desired product.

Workup

  1. temperaturebefore warming to room temperature overnight
  2. additionThen, the mixture is poured
  3. customon crushed ice
  4. extractionthe resultant solution is extracted with ethyl acetate
  5. washThe combined extracts are washed in succession with aqueous 10% Na2S2O3 solution (2×), water (3×), and brine (1×)
  6. dry with materialAfter drying (MgSO4)
  7. customthe organic solvent is evaporated
  8. stirringthe resulting slurry is stirred at 70° C. for 5 min
  9. customThe non-dissolving part is separated by filtration
  10. customdried

Sources & evidence

ORD record
ord-de05f692c3c74172bccc30bd307a1858
Source dataset
uspto-grants-2013_10
Patent number
US08551957B2

Reaction notes

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