Triethylamine → N-(2-Methoxybenzoyl)-2-bromopyrrole

HRID 1106443Notes

Reaction equation

HRID 1106443 reaction equation
[Br:1][C:2]1[NH:3][CH:4]=[CH:5][CH:6]=1.C(N(CC)CC)C.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19]>C1COCC1.C(Cl)Cl>[CH3:14][O:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([N:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[Br:1])=[O:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 122352682-Bromopyrrole

Product 1

HCID 18788312N-(2-Methoxybenzoyl)-2-bromopyrroleYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of 2-bromo-pyrrole (22.3 mmol) in 60 mL of dry THF and 120 mL of CH2Cl2 at -78° C. in an atmosphere of nitrogen, was added triethylamine (6.22 mL, 44.6 mmol) followed immediately by dropwise addition of a solution of 2-methoxybenzoyl chloride (5.0 mL, 33.6 mmol) in 40 mL CH2Cl2. The reaction mixture was stirred overnight while it was allowed to warm to room temperature. The mixture was washed with water and brine, dried (Na2SO4) and concentrated in vacuo at room temperature. The crude product was purified by chromatography on triethylamine-treated neutral silica, using EtOAc-Hex (5:95) as the eluent, to give 3.81 g of the title compound as a colorless oil. 1H NMR (CDCl3) δ: 7.58-7.36 (2 H, m), 7.10-6.86 (3 H, m), 6.36 (1 H, dd, J=3.5, 1.8), 6.16 (1 H, t, J=3.5), 3.78 (3 H, s).

Workup

  1. washThe mixture was washed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo at room temperature
  4. customThe crude product was purified by chromatography on triethylamine-
  5. additiontreated neutral silica

Sources & evidence

ORD record
ord-ff7d80dda10e4ad5b455d5800598e8f2
Source dataset
uspto-grants-2000_05
Patent number
US06057315

Reaction notes

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