2-Bromo-1-(4-hydroxyphenyl)ethanone → HCID 23248984, compound

HRID 1910946Notes

Reaction equation

HRID 1910946 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[H-].[Na+].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[O:15].[NH4+].[Cl-]>CN(C=O)C>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([C:14](=[O:15])[CH2:13][N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[C:6]([O:8][CH3:9])=[O:7])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 136930Methyl pyrrole-2-carboxylate

Product 1

HCID 23248984HCID 23248984, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a chilled solution of methyl 1H-pyrrole-2-carboxylate (1.0 g, 8.0 mmol) in dry DMF (20 mL) was added sodium hydride (60% in mineral oil, 320 mg, 8.0 mmol) portionwise. The mixture was stirred at 0° C. for 1 hour before a solution of 2-bromo-1-(4-hydroxyphenyl)ethanone (780 mg, 3.6 mmol) in DMF (5 mL) was added. The resulting yellow solution was allowed to warm to room temperature. After 2.5 hours the reaction was complete (monitored by LCMS). A saturated aqueous solution of NH4Cl (40 mL) was added and the mixture was extracted with EtOAc (1×20 mL). The organic layer was concentrated in vacuo to yield a residue that was purified by flash chromatography using the (Biotage SP4, 40 g cartridge, 0 to 100% EtOAc gradient in hexane) to give methyl 1-[2-(4-hydroxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate as a white solid (810 mg, yield 87%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EtOAc (1×20 mL)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customto yield a residue that
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-26ac103e0a4d4d8fa4a5d38ce067ddca
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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