4-Bromophenacyl bromide → 1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethanone

HRID 254414Notes

Reaction equation

HRID 254414 reaction equation
C(N(C(C)C)CC)(C)C.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=1)=[O:18].O.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([C:17](=[O:18])[CH2:16][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 74544-Bromophenacyl bromideHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 86585896Sodium bicarbonate water

Product 1

HCID 213830951-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethanoneYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (6.2 mL, 36.0 mmol) and pyrrolidine (2.3 mL, 27.6 mmol) were added to a THF (90 mL) solution of 2-bromo-1-(4-bromophenyl)ethanone (5.0 g, 18.0 mmol), and stirred at room temperature for 2 hours. Saturated sodium bicarbonate water was added to the reaction liquid, extracted with chloroform, and dried with anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (C-200, methanol:chloroform=1:99 to 3:97) to obtain the entitled compound (2.35 g, 49%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialdried with anhydrous magnesium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (C-200, methanol:chloroform=1:99 to 3:97)

Sources & evidence

ORD record
ord-f6a4a4d4c30c4ac5a0a697930d9c6476
Source dataset
uspto-grants-2011_01
Patent number
US07875633B2

Reaction notes

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