Ethyl Acetate → Methyl 5-fluoro-1-benzothiophene-2-carboxylate

HRID 1843957Notes

Reaction equation

HRID 1843957 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH3:6])=[O:4].F[C:8]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:9]=1[CH:10]=O.C(OCC)(=O)C>CC#N.CCCCCC>[F:16][C:13]1[CH:14]=[CH:15][C:8]2[S:1][C:2]([C:3]([O:5][CH3:6])=[O:4])=[CH:10][C:9]=2[CH:12]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 16907Methyl ThioglycolateHCID 1376632,5-Difluorobenzaldehyde

Product 1

HCID 22473847Methyl 5-fluoro-1-benzothiophene-2-carboxylateYield 33.89%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8058HexaneSolvent

Procedure

TEA (3.705 g, 36.619 mmol) was added to a solution of methyl 2-mercaptoacetate (3.293 g, 30.985 mmol) in CH3CN (12.5 mL). This was followed by the addition of 2,5-difluorobenzaldehyde (4 g, 28.169 mmol) in CH3CN (12.5 mL) and the resulting reaction mass was refluxed overnight under nitrogen atmosphere. The reaction was monitored by TLC (5% ethyl acetate in hexane). The reaction mass was concentrated under reduced pressure to obtain the crude product. Purification by column chromatography on silica gel (15% ethyl acetate in hexane) afforded 2 g of the product (33.89% yield).

Workup

  1. customthe resulting reaction mass
  2. temperaturewas refluxed overnight under nitrogen atmosphere
  3. concentrationThe reaction mass was concentrated under reduced pressure
  4. customto obtain the crude product
  5. customPurification by column chromatography on silica gel (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5e0a56d21a124533abfb1ce61d0ba034
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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