Acetonitrile → Ethyl 2-(p-chlorophenyl)-4,5-bis (trifluoromethyl)pyrrole-3-carboxylate

HRID 974407Notes

Reaction equation

HRID 974407 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2C(=O)O[C:17]([C:21]([F:24])([F:23])[F:22])=[N:16]2)=[CH:11][CH:10]=1.C(#N)C.Br/[C:29](=[CH:35]\[C:36]([F:39])([F:38])[F:37])/[C:30]([O:32][CH2:33][CH3:34])=[O:31]>O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[NH:16][C:17]([C:21]([F:22])([F:23])[F:24])=[C:35]([C:36]([F:39])([F:38])[F:37])[C:29]=2[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 8471TriethylamineHCID 157530294-(p-Chlorophenyl)2-trifluoromethyl-2-oxazolin-5-oneHCID 19884326ethyl (2Z)-2-bromo-4,4,4-trifluorobut-2-enoate

Product 1

HCID 54350582Ethyl 2-(p-chlorophenyl)-4,5-bis (trifluoromethyl)pyrrole-3-carboxylateYield 61.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (1.1 g, 0.011 mol) is added dropwise to a solution of 4-(p-chlorophenyl)-2-(trifluoromethyl)-2-oxazolin-5-one (2.64 g, 0.01 mol) and acetonitrile (25 mL). After stirring for 10 minutes at room temperature, a solution of ethyl 2-bromo-4,4,4-trifluorocrotonate (2.47 g, 0.01 mol) and acetonitrile (1 mL) is added dropwise to the reaction mixture. The reaction mixture is stirred at room temperature for 2 hours then poured into water and extracted with ethyl acetate. The combined organic extracts are washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give an orange oil which solidifies upon standing. Trituration with hexanes gives the title product as a yellow solid (2.36 g, 61.3%, mp 138°-140° C.).

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts are washed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give an orange oil which

Sources & evidence

ORD record
ord-cd09435b44dc4293915893fd8e7988a0
Source dataset
uspto-grants-1991_11
Patent number
US05068390

Reaction notes

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