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Benzyl Bromide → Ethyl 1-benzyl-3-(4-chloro-2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

HRID 623744
Notes
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Reaction equation

HRID 623744 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[NH:10][C:9]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:4]([F:22])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC#N>[CH2:29]([N:10]1[C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[F:22])=[C:9]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86711833ethyl 3-(4-chloro-2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 86711832Ethyl 1-benzyl-3-(4-chloro-2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342Acetonitrile
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 3-(4-chloro-2-fluorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate (1.33 g, 3.96 mmol) in dry MeCN (20 mL) was added K2CO3 (1.10 g, 7.92 mmol) and benzyl bromide (521 μL, 4.36 mmol). The reaction mixture was stirred overnight at 80° C. Addition of silica (ca. 2 g) was followed by filtration; the filtrate was concentrated in vacuo. The product was co-evaporated twice with toluene (30 mL), to result in 1.75 g (99%, 95% purity) of the desired product as a clear oil.

Workup

  1. additionAddition of silica (ca. 2 g)
  2. filtrationwas followed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f0944b3eeee144cd82b40f5fd6b4a65a
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09302988B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes