1,2-Dichloroethane → Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate

HRID 2233819Notes

Reaction equation

HRID 2233819 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=[O:9])[NH:5][C:6]=1[CH3:7].[F:11][C:12]1[C:17](O)=[C:16]([F:19])[C:15]([F:20])=[C:14]([F:21])[C:13]=1[F:22].C(Cl)CCl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][C:17]2[C:16]([F:19])=[C:15]([F:20])[C:14]([F:21])=[C:13]([F:22])[C:12]=2[F:11])=[O:9])[NH:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 685182224-Bromo-5-methyl-1H-pyrrole-2-carboxylic acid2×

Product 1

HCID 86608241Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 18, 2.16 g, 10.59 mmol) was dissolved an THF (10 ml). Pentafluorophenol and EDC (2.03 g, 10.59 mmol) were added and the mixture was stirred at room temperature for 6 h. The solvent was removed under vacuum and EtOAc (50 ml) was added. The organic phase was washed with water, 10% Na2CO3 (2×25 ml), water (50 ml) and brine (50 ml), dried over Na2SO4 and concentrated in vacuo to give the title compound as an off white solid (2.23 g).

Workup

  1. customThe solvent was removed under vacuum and EtOAc (50 ml)
  2. additionwas added
  3. washThe organic phase was washed with water, 10% Na2CO3 (2×25 ml), water (50 ml) and brine (50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfc3bb55ab7441d9bdd745ac1b62c088
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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