1,3-Dibromopropane → HCID 57517457, compound

HRID 1842449Notes

Reaction equation

HRID 1842449 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[C:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[Br:16][CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:16][CH2:17][CH2:18][CH2:19][N:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[C:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 12711558Diethyl 1H-pyrrole-2,4-dicarboxylate

Product 1

HCID 57517457HCID 57517457, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of diethyl 1H-pyrrole-2,4-dicarboxylate (2 g, 9.47 mmol) and 1,3-dibromopropane (10 mL, 98 mmol) in acetonitrile was added potassium carbonate (1.7 g, 12.3 mmol). The mixture was refluxed overnight, then filtered and concentrated to give crude diethyl 1-(3-bromopropyl)-1H-pyrrole-2,4-dicarboxylate. 1H NMR (CDCl3, 300 MHz) δ7.47 (s, 1H), 7.36 (s, 1 H), 4.47 (t, J=6.6 Hz, 2 H), 4.27 (m, 4 H), 3.32 (t, J=6.2 Hz, 2 H), 2.32 (m, 2 H), 1.34 (m, 6 H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-15c6924cbba64ef491f01512991a600a
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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