Thioglycolic Acid → 6-Bromo-1-benzothiophene-2-carboxylic acid

HRID 250280Notes

Reaction equation

HRID 250280 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](F)[C:3]=1C=O.[SH:11][CH2:12][C:13](O)=O.[OH-:16].[K+].CN(C)[CH:20]=[O:21]>>[Br:1][C:2]1[CH:3]=[CH:6][C:7]2[CH:8]=[C:9]([C:20]([OH:21])=[O:16])[S:11][C:12]=2[CH:13]=1

Participants

5

Reactant 4

HCID 1133Thioglycolic AcidHCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 224739772-Bromo-6-fluorobenzaldehyde

Product 1

HCID 135679806-Bromo-1-benzothiophene-2-carboxylic acidYield 76%

Conditions

Temperature
138 °C

Procedure

A stirred solution of 2-bromo-6-fluorobenzaldehyde (2.3 Kg, 11.33 moles) and mercaptoacetic acid (1.04 Kg, 11.33 mole) is added to a solution of KOH (951 g, 16.99 mol) in dimethylformamide (11.0 L) at room temperature. The reaction mixture is stirred for 1.5 h at 136 to 140° C. Upon completion of the reaction, the reaction mixture is cooled to 10° C. and quenched with concentrated HCl (2.5 L). The mixture is stirred for 1 h at 10° C. and the resulting solid is filtered. The filtered cake is washed with water (2×3 L) and dried under vacuum to afford the title compound (2.2 Kg, 76%) as a yellow solid.

Workup

  1. customUpon completion of the reaction
  2. temperaturethe reaction mixture is cooled to 10° C.
  3. customquenched with concentrated HCl (2.5 L)
  4. stirringThe mixture is stirred for 1 h at 10° C.
  5. filtrationthe resulting solid is filtered
  6. washThe filtered cake is washed with water (2×3 L)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6c0ef3a8d7024fd6b64c5835ee00b9a2
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

Loading…