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

HRID 2282125Notes

Reaction equation

HRID 2282125 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-7492c3586c484938927121df55653202
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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