Methyl Thioglycolate → Methyl 5-bromo-6-fluorobenzo[b]thiophene-2-carboxylate

HRID 523571Notes

Reaction equation

HRID 523571 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=O.[CH3:12][O:13][C:14](=[O:17])[CH2:15][SH:16]>CS(C)=O>[Br:1][C:2]1[C:3]([F:11])=[CH:4][C:5]2[S:16][C:15]([C:14]([O:13][CH3:12])=[O:17])=[CH:7][C:6]=2[CH:9]=1

Participants

4

Reactant 2

HCID 16907Methyl ThioglycolateHCID 222607695-Bromo-2,4-difluorobenzaldehyde

Product 1

HCID 70983611Methyl 5-bromo-6-fluorobenzo[b]thiophene-2-carboxylateYield 5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Using analogous reaction condition and reagents as described in Example 25 for the preparation of I-25a above, 5-bromo-2,4-difluorobenzaldehyde (I-28a: 475 mg, 2.149 mmol) was reacted with TEA (0.748 mL, 5.372 mmol), mercapto-acetic acid methyl ester (0.211 mL, 2.36 mmol) and DMSO (4 mL) to afford crude product. Purification by column chromatography on silica gel (1.5% ethyl acetate in hexane) afforded 30 mg of the product (5% yield).

Workup

  1. customto afford crude product
  2. customPurification by column chromatography on silica gel (1.5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-58ce70c9b93d4d37a824c294911e098c
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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