Iodine → HCID 66776531, compound

HRID 1616093Notes

Reaction equation

HRID 1616093 reaction equation
[NH:1]([C:5]1[CH:6]=[C:7]([S:13](Cl)(=O)=O)[C:8]([CH3:12])=[CH:9][C:10]=1[F:11])[C:2]([CH3:4])=[O:3].II>C(O)(=O)C>[NH:1]([C:5]1[C:10]([F:11])=[CH:9][C:8]([CH3:12])=[C:7]([SH:13])[CH:6]=1)[C:2]([CH3:4])=[O:3]

Participants

4

Reactant 2

HCID 807IodineHCID 86662547HCID 86662547, compound

Product 1

HCID 66776531HCID 66776531, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Acetamino-4-fluoro-6-methyl-phenylsulfonylchloride (500 g, 1.89 mol) was dissolved in 2 L of acetic acid. Red phosphorus (100 g, 3.22 mmol) and iodine (10 g, 39 mmol) were added to the solution, and the mixture was refluxed for 3 hours. The acetic acid was removed under reduced pressure, water was added and the residue extracted with ethyl acetate. The organic phase was dried with sodium sulfate and concentrated under reduced pressure to give 5-acetamino-4-fluoro-2-methyl-benzenethiol as a crude intermediate (270 g, 72%).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe acetic acid was removed under reduced pressure, water
  3. additionwas added
  4. extractionthe residue extracted with ethyl acetate
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a6522ac216949a5aa75ae932b72183b
Source dataset
uspto-grants-2014_07
Patent number
US08765774B2

Reaction notes

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