Acetonitrile → HCID 117662385, compound

HRID 1428390Notes

Reaction equation

HRID 1428390 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[NH:9][C:10](=[O:13])[O:11][CH3:12].CC#N.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[I:29]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[F:1][C:2]1[C:7]([I:29])=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[NH:9][C:10](=[O:13])[O:11][CH3:12]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 120273N-IodosuccinimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 22078400HCID 22078400, compound

Product 1

HCID 117662385HCID 117662385, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of methyl (2-fluoro-6-hydroxyphenyl)carbamate (1.06 g) and MeCN (90 mL) was added p-toluenesulfonic acid monohydrate (1.09 g), followed by stirring at room temperature for 5 minutes. To the reaction mixture was added N-iodosuccinimide (1.29 g), followed by stirring at room temperature overnight. The reaction mixture was diluted with chloroform, and washed with a 10% aqueous sodium thiosulfate solution and brine in this order. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=85/15-75/25) to obtain methyl (2-fluoro-6-hydroxy-3-iodophenyl)carbamate (408 mg).

Workup

  1. stirringby stirring at room temperature overnight
  2. washwashed with a 10% aqueous sodium thiosulfate solution and brine in this order
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=85/15-75/25)

Sources & evidence

ORD record
ord-2fe4ad7cd422462e8b2e19a98ff6f850
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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