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

HRID 623779Notes

Reaction equation

[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[C:14]([CH3:15])=[C:13]([C:16]([F:19])([F:18])[F:17])[NH:12][C:11]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].C([O-])([O-])=O.[K+].[K+]>C(#N)C.CCOC(C)=O.O>[CH2:1]([N:12]1[C:13]([C:16]([F:19])([F:17])[F:18])=[C:14]([CH3:15])[C:10]([Br:9])=[C:11]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Benzyl bromide (10.9 mL, 91.66 mmol) was added to the solution of crude ethyl 3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate (25 g, 83.33 mmol) and K2CO3 (23.03 g, 166.66 mmol) in acetonitrile. The reaction mixture was stirred for 13 h at 80° C. Then the reaction mixture was cooled to RT and then diluted with EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×400 mL). Combined organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to yield crude mass which was then purified by column chromatography (100-200 mesh Silica gel; 10% ethyl acetate/hexane; Rf-value 0.8) to afford title compound (29 g, 89.18% yield, pale yellow color oil).

Workup

temperatureThen the reaction mixture was cooled to RT
extractionThe aqueous layer was extracted with EtOAc (2×400 mL)
dry with materialCombined organic layer was dried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure
customto yield crude mass which
customwas then purified by column chromatography (100-200 mesh Silica gel; 10% ethyl acetate/hexane; Rf-value 0.8)

Sources & evidence

ORD record: ord-8b724a8843334160a54ac07f9bcc9f9f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302988B2

Reaction notes

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