N-Iodosuccinimide → HCID 66643942, compound

HRID 1848513Notes

Reaction equation

HRID 1848513 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[I:12]N1C(=O)CCC1=O>FC(F)(F)S(O)(=O)=O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[I:12]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 6031445-Bromophthalide

Product 1

HCID 66643942HCID 66643942, compound

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

To a cooled (0° C.) solution of 5-bromo-2-benzofuran-1(3H)-one (50 g, 0.235 mol) in trifluoromethanesulfonic acid (400 mL) was added N-iodosuccinimide (55.5 g, 0.247 mol). The resulting mixture was stirred at room temperature overnight, then poured slowly into ice water (2 L), filtered and the filtrate extracted with EtOAc. The combined organic layers were washed with water and brine, dried and concentrated to give 5-bromo-4-iodo-2-benzofuran-1(3H)-one.

Workup

  1. filtrationfiltered
  2. extractionthe filtrate extracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d8e78d07899c413f8c77bc5bfc1090f7
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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