Iodine → HCID 66603717, compound

HRID 1627929Notes

Reaction equation

HRID 1627929 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][O:7]2.[I:12]I>CO.[N+]([O-])([O-])=O.[Ag+]>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]([I:12])[CH2:5][CH2:6][O:7]2

Participants

5

Reactant 2

HCID 807IodineHCID 15758918HCID 15758918, compound

Product 1

HCID 66603717HCID 66603717, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-chlorochroman (0.101 g; 0.6 mmol) and silver nitrate (0.112 g; 0.66 mmol) in methanol (6 mL) was added iodine (0.153 g; 0.6 mmol) and the reaction mixture for 30 min. The reaction was quenched by adding a solution of sodium thiosulphate 0.5M (2.5 mL) and the aqueous layer was extracted with ethyl acetate. The organics were combined, dried over sodium sulphate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-80%) in heptane furnished 0.088 g (50%) of 5-chloro-4-iodochroman.

Workup

  1. customThe reaction was quenched
  2. additionby adding a solution of sodium thiosulphate 0.5M (2.5 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (5-80%) in heptane

Sources & evidence

ORD record
ord-aa8aa0fcb5854bfba364296732a5257e
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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