Sodium Thiosulfate → 4-Amino-3-fluoro-5-iodobenzonitrile

HRID 2423347

Reaction equation

HRID 2423347 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[F:10].[I:11]Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[NH2:1][C:2]1[C:9]([I:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[F:10]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 24640Iodine chlorideHCID 27564314-Amino-3-fluorobenzonitrile

Product 1

HCID 442031204-Amino-3-fluoro-5-iodobenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25 ml of two-neck round bottom flask was filled with argon gas and the solution of 4-amino-3-fluoro-benzonitrile (300 mg, 2.204 mmol, 1 equiv.) in methylenechloride was put into the flask. To the solution was added iodomonochloride (393.6 mg, 2.424 mmol, 1.1 equiv.) and stirred for 1 hour. After confirming the completion of the reaction with TLC, to resulting solution was added saturated sodium thiosulphate solution and stirred. The reaction solution was extracted with methylenechloride, washed with water(twice) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The obtained liquid was column-chromatographed (n-hexane/ethylacetate=3/1) to yield a brown liquid.

Workup

  1. additionA 25 ml of two-neck round bottom flask was filled with argon gas
  2. customthe completion of the reaction with TLC
  3. customto resulting solution
  4. stirringstirred
  5. extractionThe reaction solution was extracted with methylenechloride
  6. washwashed with water(twice) and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained liquid was column-chromatographed (n-hexane/ethylacetate=3/1)
  11. customto yield a brown liquid

Sources & evidence

ORD record
ord-3323ce58260142188affe4053a67c887
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Linked notes

Loading…