Bromomethyl 4-methoxyphenyl ketone → HCID 67365424, compound

HRID 77354Notes

Reaction equation

HRID 77354 reaction equation
[Br:1][C:2]1[NH:6][C:5]([C:7]([O:9][CH2:10]C)=[O:8])=[CH:4][CH:3]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:10][O:9][C:7]([C:5]1[N:6]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:15])[C:2]([Br:1])=[CH:3][CH:4]=1)=[O:8]

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 11430Potassium CarbonateHCID 59559613ethyl 5-bromo-1H-pyrrole-2-carboxylate

Product 1

HCID 67365424HCID 67365424, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 5-bromo-1H-pyrrole-2-carboxylate (0.13 g, 0.64 mmol), 2-bromo-1-(4-methoxyphenyl)ethanone (160 mg, 0.69 mmol) and potassium carbonate (132 mg, 0.95 mmol) in N,N-dimethylformamide (4 mL) was stirred at room temperature overnight. At this time, the light brown reaction mixture was quenched with water. The resulting precipitate was collected by filtration and dried in vacuo. The resulting solid was dissolved in methylene chloride, concentrated in vacuo and then triturated with diethyl ether. The resulting solid was collected by filtration and dried in vacuo to afford 5-bromo-1-[2-(4-methoxy-phenyl)-2-oxo-ethyl]-1H-pyrrole-2-carboxylic acid methyl ester (155 mg, 69%) as light brown solid. 1H NMR (chloroform-d) δ ppm 8.00 (d, J=8.8 Hz, 2H), 6.96-7.07 (m, 3H), 6.85 (d, J=1.8 Hz, 1H), 5.71 (s, 2H), 3.91 (s, 3H), 3.75 (s, 3H).

Workup

  1. customAt this time, the light brown reaction mixture was quenched with water
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried in vacuo
  4. dissolutionThe resulting solid was dissolved in methylene chloride
  5. concentrationconcentrated in vacuo
  6. customtriturated with diethyl ether
  7. filtrationThe resulting solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-835237f0d9e14a5ca87c545061af1202
Source dataset
uspto-grants-2014_09
Patent number
US08841299B2

Reaction notes

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