Potassium Carbonate → Ethyl 3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

HRID 623778Notes

Reaction equation

HRID 623778 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:11]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH:13][C:14]=1[C:15]([F:18])([F:17])[F:16].C([O-])([O-])=O.[K+].[K+]>C(#N)C.CCOC(C)=O.O>[Br:1][C:11]1[C:10]([CH3:9])=[C:14]([C:15]([F:18])([F:16])[F:17])[NH:13][C:12]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 71502098ethyl 4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 86711863Ethyl 3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Bromosuccinimide (NBS) (17.7 g, 99.77 mmol) was portion wise added to an ice cooled solution of ethyl 4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate (21 g, 95.02 mmol) and K2CO3 (13.7 g, 99.77 mmol) in acetonitrile. The reaction mixture was stirred for 2 h at RT. The reaction mixture was diluted with EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×300 mL). Combined organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to yield crude mass which was directly used to next step without further purification

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (2×300 mL)
  2. dry with materialCombined organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto yield crude mass which
  5. customwas directly used to next step without further purification

Sources & evidence

ORD record
ord-21b61af4ef304239b641eb2178f1323f
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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