Sodium Carbonate → methyl 5-bromo-1-benzothiophene-2-carboxylate

HRID 1785819Notes

Reaction equation

HRID 1785819 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=O.[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][SH:13].C([O-])([O-])=O.[Na+].[Na+]>CO.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:13][C:12]([C:11]([O:15][CH3:16])=[O:14])=[CH:7][C:6]=2[CH:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 16907Methyl ThioglycolateHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 2824065methyl 5-bromo-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 5-bromo-2-fluorobenzaldehyde (6 g, 29.6 mmol), methyl thioglycolate (2.64 mL, 29.6 mmol), and Na2CO3 (3.14 g, 29.6 mmol) in methanol was heated to reflux for 1 hour, poured into brine, and extracted with ethyl acetate (3×). The combined extracts were washed with brine and filtered through silica gel to provide the desired product. MS (ESI(−)) m/e 270 (M−H)−.

Workup

  1. temperatureto reflux for 1 hour
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined extracts were washed with brine
  4. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-ff58bdda35fa4fc8baad8369ffce01c0
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

Loading…