N-Iodosuccinimide → HCID 66643942, compound

HRID 2281322Notes

Reaction equation

HRID 2281322 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 commercially available 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-c4ed942b70634dc2880e8fe9b9ca70c6
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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