Water → HCID 43227580, compound

HRID 2114340Notes

Reaction equation

HRID 2114340 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)=[O:4].[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.O>CCOCC>[Br:11][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-one

Product 1

HCID 43227580HCID 43227580, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2-bromo-1-(3-bromophenyl)ethanone (4.0 g, 14.39 mmol) in anhydrous ether (50 mL) was added dropwise to a solution of pyrrolidine (2.05 g, 28.78 mmol) in anhydrous ether (20 mL) at 0° C. The reaction mixture was then warmed to room temperature. After stirring for 2 h, water (80 mL) was added and the aqueous layer was extracted with ethyl acetate (2×80 mL). The combined organic layers were dried over MgSO4 and concentrated to yield 1-(3-bromophenyl)-2-(1-pyrrolidinyl)ethanone as a light yellow oil (3.6 g, 94%), which was used without purification. MS (ES) m/e 268 [M+H]+.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate (2×80 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bce98c66f3cb452ca064a5777bd0bf29
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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