Bromomethyl 4-methoxyphenyl ketone → HCID 67367511, compound

HRID 1910917Notes

Reaction equation

HRID 1910917 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[NH:5][CH:6]=1.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:14].CC(C)([O-])C.[K+]>CN(C=O)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH2:12][N:5]2[CH:6]=[CH:2][CH:3]=[C:4]2[C:7]([O:9][CH3:10])=[O:8])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 2763594Methyl 4-bromo-1H-pyrrole-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67367511HCID 67367511, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 4-bromo-1H-pyrrole-2-carboxylate (1 g, 4.9 mmol) and 2-bromo-1-(4-methoxyphenyl)ethanone (1.23 g, 5.3 mmol) in DMF (30 mL) was added potassium tert-butoxide (0.60 g, 5.4 mmol) portionwise at −15° C. The mixture was stirred at that temperate for 15 minutes and then at room temperature for 1 hour. The mixture was quenched with aqueous HCl (1M) and then extracted with EtOAc (3×100 mL). The organic layers were washed with brine, water and then concentrated in vacuo to give a liquid. This was azeotroped with toluene to give a residue corresponding to methyl 1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate. ESI-MI m/z [M+H]+ 353.8. The crude was used in the next step without purification

Workup

  1. waitat room temperature for 1 hour
  2. customThe mixture was quenched with aqueous HCl (1M)
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe organic layers were washed with brine, water
  5. concentrationconcentrated in vacuo
  6. customto give a liquid
  7. customThis was azeotroped with toluene

Sources & evidence

ORD record
ord-d1799db731904d3da9cfb09c4ec2534f
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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