N-bromobutanimide → 1-(4-Bromo-1-methyl-1H-pyrrol-2-yl)-2,2,2-trichloro-1-ethanone

HRID 632965Notes

Reaction equation

HRID 632965 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Cl:9][C:10]([Cl:20])([Cl:19])[C:11]([C:13]1[N:14]([CH3:18])[CH:15]=[CH:16][CH:17]=1)=[O:12]>C1COCC1>[Br:8][C:16]1[CH:17]=[C:13]([C:11](=[O:12])[C:10]([Cl:9])([Cl:19])[Cl:20])[N:14]([CH3:18])[CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27771642,2,2-Trichloro-1-(1-methyl-1H-pyrrol-2-yl)-1-ethanone

Product 1

HCID 112897251-(4-Bromo-1-methyl-1H-pyrrol-2-yl)-2,2,2-trichloro-1-ethanoneYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NBS (N-Bromosuccinimide, 2.36 g, 13.24 mmol, 1.0 equiv.) was added to a stirred solution of 2-(trichloroacetyl)-1-methylpyrrole (2) (3 g, 13.24 mmol, 1.0 equiv.) in anhydrous THF (35 mL) at −10° C. The reaction mixture was kept at −10° C. for 2 hours and then left to reach room temperature (ca. 4 hours). Excess THF was evaporated in vacuum and the solid was re-dissolved in a mixture of EtOAc/n-hexane (1:9). The resulting mixture was filtered through a plug of silica, and the filtrate was evaporated in vacuo. The resulting solid was recrystallised from n-hexane to give 3 (3.55 g, 88%). IR (FTIR, vmax/cm−1): 3148, 2956, 1669 (C═O), 1458, 1215, 1189, 1062, 923, 842, 823, 748, 678; 1H-NMR (CDCl3, 400 MHz) δ 7.46 (1H, d, J=2.0 Hz), 6.95 (1H, d, J=1.6 Hz) 3.95 (3H, s); 13C NMR (CDCl3, 100 MHz): δ 172.4, 132.8, 124.6, 132.2, 96.1, 38.7; EIMS m/z (+EI) calc. for C7H5BrCl3NO (M)+ 305.38, LCMS analysis found 306.86 (M+H)+

Workup

  1. waitleft
  2. customto reach room temperature
  3. custom(ca. 4 hours)
  4. customExcess THF was evaporated in vacuum
  5. dissolutionthe solid was re-dissolved in a mixture of EtOAc/n-hexane (1:9)
  6. filtrationThe resulting mixture was filtered through a plug of silica
  7. customthe filtrate was evaporated in vacuo
  8. customThe resulting solid was recrystallised from n-hexane

Sources & evidence

ORD record
ord-8c8ea1a229ea4d8091570cc7337f840b
Source dataset
uspto-grants-2016_04
Patent number
US09321774B2

Reaction notes

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