Bromine → ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate

HRID 912586Notes

Reaction equation

HRID 912586 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:13]Br>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:13][C:6]1[C:2]([CH3:1])=[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[NH:4][C:5]=1[CH3:7]

Participants

5

Reactant 2

HCID 24408BromineHCID 1374771H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl ester

Product 1

HCID 138486ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate (3.42 g, 20 mmol) in carbon tetrachloride (40 mL) was added a solution of bromine in carbon tetrachloride (10 mL) dropwise at 20° C. After the addition was complete, stirring was continued for 2 h. The reaction mixture was diluted with DCM, washed with aqueous NaHCO3 and water, and then dried over Na2SO4. Evaporation of solvent gave ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate as a solid (4.8 g), which was used in the next step without purification. 1H-NMR (CDCl3): δ 9.36 (1H, s), 4.30 (2H, q), 2.28 (3H, s), 2.26 (3H, s), 1.36 (3H, t).

Workup

  1. additionAfter the addition
  2. washwashed with aqueous NaHCO3 and water
  3. dry with materialdried over Na2SO4
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-c42fdd84f13e4bc9a801ccb67316cb09
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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