Water → 5-Bromo-4-cyano-3-(2,4-dichlorophenyl)thiophene-2-carboxylic acid

HRID 2402452Notes

Reaction equation

HRID 2402452 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9]CC)=[O:8])=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[C:3]=1[C:20]#[N:21].O.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])[C:3]=1[C:20]#[N:21]

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 66855139Ethyl 5-bromo-4-cyano-3-(2,4-dichlorophenyl)thiophene-2-carboxylate

Product 1

HCID 668554875-Bromo-4-cyano-3-(2,4-dichlorophenyl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-bromo-4-cyano-3-(2,4-dichlorophenyl)thiophene-2-carboxylate (4.60 g, 0.0114 mol) was dissolved in Tetrahydrofuran (100 mL) and Water (20 mL) and 1.00 M of Sodium hydroxide in Water (34.1 mL, 0.0341 mol) was added The mixture was stirred at room temperature overnight. Reaction was quenched by addition of 1N HCl (36 mL), extracted with EA (3×), dried MgSO4, filtered and evaporated to give the product that was used without further purification (4.28 g, 100%). LCMS: (FA) ES−, 374, 376, 378. 1H NMR (400 MHz, d1-chloroform) δ: 7.52 (d, J=1.99 Hz, 1H), 7.35 (dd, J=8.28, 2.02 Hz, 1H), 7.21 (d, J=8.27 Hz, 1H).

Workup

  1. customReaction
  2. customwas quenched by addition of 1N HCl (36 mL)
  3. extractionextracted with EA (3×), dried MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give the product that
  7. customwas used without further purification (4.28 g, 100%)

Sources & evidence

ORD record
ord-35ffd5711afc4b59b8be24ab35f61b29
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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