Methyl Thioglycolate → Methyl 6-bromo-5-fluorobenzothiophene-2-carboxylate

HRID 572408Notes

Reaction equation

HRID 572408 reaction equation
[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=O)=[C:4](F)[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:4]2[CH:3]=[C:2]([Br:1])[C:9]([F:10])=[CH:8][C:5]=2[CH:6]=1)=[O:17]

Participants

4

Reactant 2

HCID 16907Methyl ThioglycolateHCID 224890814-Bromo-2,5-difluorobenzaldehyde

Product 1

HCID 70982166Methyl 6-bromo-5-fluorobenzothiophene-2-carboxylateYield 102.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using analogous reaction condition and reagents as described in Example 25 for the preparation of I-25a above, 4-bromo-2,5-difluoro-benzaldehyde (I-27a: 1.71 g, 7.73 mmol) was reacted with TEA (1.4 mL, 10.05 mmol), mercapto-acetic acid methyl ester (920 mg, 8.51 mmol) and acetonitrile (50 mL) to afford crude product. Purification by column chromatography on silica gel (5% ethyl acetate in hexane) afforded 2.3 g of the product (Yield 64%).

Workup

  1. customto afford crude product
  2. customPurification by column chromatography on silica gel (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-ee6f9e3848704f6c929092c05d5a7af7
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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