1,2-Dibromoethane → diethyl 1-(2-bromoethyl)-1H-pyrrole-2,4-dicarboxylate

HRID 1842446Notes

Reaction equation

HRID 1842446 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]Br.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:16][CH2:17][CH2:18][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 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 12711558Diethyl 1H-pyrrole-2,4-dicarboxylate

Product 1

HCID 18967495diethyl 1-(2-bromoethyl)-1H-pyrrole-2,4-dicarboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of diethyl 1H-pyrrole-2,4-dicarboxylate (0.7 g, 3.31 mmol), and 1,2-dibromoethane (2.8 mL, 32.5 mmol) in MeCN (30 mL) was added K2CO3 (0.55 g, 39.7 mmol). This reaction mixture was refluxed overnight then filtered. The filtrate was collected and concentrated to give diethyl 1-(2-bromoethyl)-1H-pyrrole-2,4-dicarboxylate (0.8 g, 76%). 1H NMR (CDCl3, 300 MHz) δ7.42 (d, J=1.8 Hz, 1 H), 7.33 (d, J=1.8 Hz, 1 H), 4.60 (t, J=6.0 Hz, 2 H), 4.22 (q, J=7.2 Hz, 4 H), 3.62 (t, J=6.4 Hz, 2 H), 1.28 (m, 6 H).

Workup

  1. temperatureThis reaction mixture was refluxed overnight
  2. filtrationthen filtered
  3. customThe filtrate was collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6f5357bd7cf247beb8f5525888003b9d
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

Loading…