Methyl Thioglycolate → Methyl 6-bromo-4-fluoro-1-benzothiophene-2-carboxylate

HRID 523561Notes

Reaction equation

HRID 523561 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.[CH3:12][O:13][C:14](=[O:17])[CH2:15][SH:16]>C(#N)C>[CH3:12][O:13][C:14]([C:15]1[S:16][C:8]2[CH:9]=[C:2]([Br:1])[CH:3]=[C:4]([F:11])[C:5]=2[CH:6]=1)=[O:17]

Participants

4

Reactant 2

HCID 16907Methyl ThioglycolateHCID 27732904-Bromo-2,6-difluorobenzaldehyde

Product 1

HCID 19007547Methyl 6-bromo-4-fluoro-1-benzothiophene-2-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using analogous reaction condition and reagents as described in Example 25 for the preparation of I-25a, 4-bromo-2,6-difluoro-benzaldehyde (I-26a: 2.8 g, 12.8 mmol) was reacted with TEA (1.66 g, 16.47 mmol), mercapto-acetic acid methyl ester (1.47 g, 13.83 mmol) and acetonitrile (50 mL) to afford crude product. Purification by column chromatography on silica gel (2% ethyl acetate in hexane) afforded 2.3 g of the product (64% yield).

Workup

  1. customto afford crude product
  2. customPurification by column chromatography on silica gel (2% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-74292f6c9e9249aea4901f8cd43d5294
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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