Acetonitrile → HCID 117662396, compound

HRID 1428385Notes

Reaction equation

HRID 1428385 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.[Cl:29]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:29][C:7]1[C:2]([F:1])=[C:3]([NH:9][C:10](=[O:13])[O:11][CH3:12])[C:4]([OH:8])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 31398ChlorosuccinimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 22078400HCID 22078400, compound

Product 1

HCID 117662396HCID 117662396, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of methyl (2-fluoro-6-hydroxyphenyl)carbamate (346 mg) and MeCN (30 mL) was added p-toluenesulfonic acid monohydrate (711 mg), followed by stirring at room temperature for 5 minutes. To the reaction mixture was added N-chlorosuccinimide (250 mg), 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=80/20-70/30) to obtain methyl (3-chloro-2-fluoro-6-hydroxyphenyl)carbamate (173 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=80/20-70/30)

Sources & evidence

ORD record
ord-59e263d6a26a437ba46a46aa9268aebc
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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