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

HRID 2114333Notes

Reaction equation

HRID 2114333 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C(OCC)C>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 74544-Bromophenacyl bromideHCID 31268Pyrrolidine

Product 1

HCID 213830951-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethanoneYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

2-bromo-1-(4-bromophenyl)ethanone (5.0 g, 18 mmol) was dissolved in 10 mL diethyl ether and added dropwise over 15 min to a solution of pyrrolidine (3.0 mL, 36 mmol) in 20 mL diethyl ether cooled to 0° C. in an ice bath. The resulting solution was allowed to warm to room temperature and maintained for 1 h. The solvent was removed under reduced pressure. The residue was dissolved in 100 mL of EtOAc and washed with sodium bicarbonate (100 mL) and then brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give 4.6 g (96%) of the title compound as a yellow/orange solid. MS (ES) m/e 268/270 [M+H]+.

Workup

  1. temperatureto warm to room temperature
  2. temperaturemaintained for 1 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in 100 mL of EtOAc
  5. washwashed with sodium bicarbonate (100 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e97c3a014d746f28cba08b77b7607fb
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

Loading…