Hydrochloric Acid → 1-Benzyl-3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid

HRID 623780Notes

Reaction equation

HRID 623780 reaction equation
O.[OH-].[Li+].[CH2:4]([N:11]1[C:15]([C:16]([F:19])([F:18])[F:17])=[C:14]([CH3:20])[C:13]([Br:21])=[C:12]1[C:22]([O:24]CC)=[O:23])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>C1COCC1.O>[CH2:4]([N:11]1[C:15]([C:16]([F:17])([F:18])[F:19])=[C:14]([CH3:20])[C:13]([Br:21])=[C:12]1[C:22]([OH:24])=[O:23])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86711864Ethyl 1-benzyl-3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 867118651-Benzyl-3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acidYield 85.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (8.89 g, 371.6 mmol) was added to the ice cold solution of ethyl 1-benzyl-3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate (29 g, 74.32 mmol) in THF (300 mL) and H2O (100 mL) warmed to RT and then heated at 100° C. for 14 h, cooled to RT and then diluted with H2O and acidify with 6N HCl (pH-2). The aqueous layer was extracted with EtOAc (2×350 mL). Combined organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to yield crude mass which was triturated with diethyl ether to afford title compound (23 g, 85.48% yield, white color solid).

Workup

  1. temperatureheated at 100° C. for 14 h
  2. temperaturecooled to RT
  3. extractionThe aqueous layer was extracted with EtOAc (2×350 mL)
  4. dry with materialCombined organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto yield crude mass which
  7. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-3aa9920747214732a011c81784a7b4f6
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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