Benzyl Bromide → HCID 86711816, compound

HRID 623727Notes

Reaction equation

HRID 623727 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[CH:11][NH:10][C:9]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[CH2:21]([N:10]1[CH:11]=[C:12]([CH3:13])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 14462625HCID 14462625, compound

Product 1

HCID 86711816HCID 86711816, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Ethyl 3-(4-chlorophenyl)-4-methyl-1H-pyrrole-2-carboxylate (9 g, 34.1 mmol) was dissolved in dry DMF (20 mL). At 0° C., 60% NaH in mineral oil (1.365 g, 34.1 mmol) was added. After 20 min gas evolution had ceased and benzyl bromide (4.08 mL, 34.1 mmol) was added. The reaction mixture was stirred at room temperature overnight. Brine (400 mL) was added, followed by EtOAc (400 mL). The organic layer was washed with H2O (2×400 mL), brine (400 mL), dried (Na2SO4) and evaporated under reduced pressure. The product was purified by column chromatography (silica, heptane/EtOAc, 9:1), to yield 8.40 g (70%) of the desired product.

Workup

  1. washThe organic layer was washed with H2O (2×400 mL), brine (400 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated under reduced pressure
  4. customThe product was purified by column chromatography (silica, heptane/EtOAc, 9:1)

Sources & evidence

ORD record
ord-d30dc630380247a19e8cddb2ccb2b199
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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