Benzyl Bromide → HCID 976942, compound

HRID 1854677Notes

Reaction equation

HRID 1854677 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([OH:12])[CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O>[CH2:21]([O:12][C:6]1[CH:5]=[C:4]([N:3]([CH2:1][CH3:2])[CH2:13][CH3:14])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 872934-(Diethylamino)-2-hydroxybenzaldehyde

Product 1

HCID 976942HCID 976942, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 4-diethylamino-2-hydroxybenzaldehyde (300 mg, 1.55 mmol) and potassium carbonate (0.43 g, 3.1 mmol) in 1.6 mL of acetone was added benzyl bromide (300 mg, 1.55 mmol) at 0° C. After being stirred at room temperature overnight, the reaction mixture was filtered to remove inorganic salts. The filtrate was diluted with diethyl ether, and the solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10) to obtain the title compound as a yellow oil (292 mg, 67%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove inorganic salts
  3. additionThe filtrate was diluted with diethyl ether
  4. washthe solution was washed with saturated NaHCO3 aqueous solution, brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10)

Sources & evidence

ORD record
ord-0c85831f21f94a31aee16727f04bff35
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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