Water → HCID 59291560, compound

HRID 383924Notes

Reaction equation

HRID 383924 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[CH:10][C:11]=2[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Cl:23])C(=O)C1.Cl(O)(=O)(=O)=O.O>C(Cl)(Cl)Cl>[Cl:23][C:9]1[S:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24247Perchloric AcidHCID 31398ChlorosuccinimideHCID 12486141HCID 12486141, compound

Product 1

HCID 59291560HCID 59291560, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-phenylthiophene-3-carboxylate and NCS in CHCl3 was added perchloric acid, followed by stirring at 50° C. for overnight. To the reaction mixture was added water, and the aqueous layer was extracted with EtOAc. The organic layer was washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure. The residue obtained was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc) to obtain methyl 5-chloro-2-phenylthiophene-3-carboxylate as a white solid.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe organic layer was washed with water and brine in this order
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc)

Sources & evidence

ORD record
ord-ffd1a2e86ca949548de5b6901c3b5871
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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