Potassium Carbonate → 6-Chloro-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 493214Notes

Reaction equation

HRID 493214 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][SH:21]>CS(C)=O>[CH3:24][O:23][C:19]([C:20]1[S:21][C:4]2[CH:3]=[C:2]([Cl:1])[C:9]([O:10][CH3:11])=[CH:8][C:5]=2[CH:6]=1)=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 149282684-Chloro-2-fluoro-5-methoxybenzaldehyde

Product 1

HCID 688807806-Chloro-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-chloro-2-fluoro-5-methoxybenzaldehyde (0.821 g, 4.35 mmol) in 8.7 mL of DMSO were successively added K2CO3 (1.81 g, 3 eq.) and methyl thioglycolate (0.474 mL, 1.2 eq.), and the mixture was vigorously stirred at 50° C. for 2 h. After cooling, the reaction mixture was poured onto crashed ice/HCl, twofold extracted with AcOEt, washed with water, dried over sodium sulfate, and evaporated. Flash chromatography (SiO2, hexane/AcOEt=85/15), followed by crystallization from heptane/AcOEt, yielded 0.300 g of the title compound as off-white solid.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured
  3. extractiontwofold extracted with AcOEt
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customFlash chromatography (SiO2, hexane/AcOEt=85/15), followed by crystallization from heptane/AcOEt

Sources & evidence

ORD record
ord-cd34385ba4f74eed82e17c07a4fda942
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

Loading…