Potassium Carbonate → Pyrrolidine, 1-(2-(m-bromophenoxy)ethyl)-

HRID 273520Notes

Reaction equation

HRID 273520 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 816691-(2-Chloroethyl)pyrrolidine

Product 1

HCID 211452Pyrrolidine, 1-(2-(m-bromophenoxy)ethyl)-Yield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-bromo-phenol (5.34 g, 30.9 mmol, 1 equiv), 1-(2-chloro-ethyl)-pyrrolidine (5.24 g, 30.9 mmol, 1 equiv) and potassium carbonate (K2CO3) (34 g, 24.7 mmol, 8 equiv) were weighed out into a 500 mL round bottom flask, were diluted with 150 mL DMF and stirred for 2 days. The contents were poured onto ethyl acetate water mixture and extracted once. The organic layer was separated, washed with brine and dried over sodium sulfate (Na2SO4). Filtration followed by concentration provided crude product as a pale yellow oil. Column chromatography (1:9 ethyl acetate/hexanes) provided desired product as a yellow oil (3.6 g, 43% yield). 1H NMR (DMSO-d6): δ 1.65-1.69 (m, 4H), 2.72 (s, 1H), 2.75 (t, J=5.8 Hz, 2H), 2.88 (s, 1H), 4.06 (t, J=5.8 Hz, 2H), 6.95 (dd, J=8.35 Hz, 1H), 7.11 (d, J=7.7, 1H), 7.13-7.14 (m, 1H), 7.22 (t, J=8.1 Hz, 1H).

Workup

  1. additionThe contents were poured onto ethyl acetate water mixture
  2. extractionextracted once
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate (Na2SO4)
  6. filtrationFiltration
  7. concentrationfollowed by concentration
  8. customprovided crude product as a pale yellow oil

Sources & evidence

ORD record
ord-7d54b8fa887d4b1289471392838182bc
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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