Benzyl Bromide → HCID 85975948, compound

HRID 1622108Notes

Reaction equation

HRID 1622108 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:13]=[O:14])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[K+]>CC(C)=O>[CH2:15]([O:12][C:11]1[C:10]([CH:13]=[O:14])=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Br:1])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 516893Potassium BicarbonateHCID 71711084Methyl 3-bromo-5-formyl-4-hydroxybenzoate

Product 1

HCID 85975948HCID 85975948, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 3-bromo-5-formyl-4-hydroxybenzoate (11.5 g, 44.39 mmol) was dissolved in acetone (100 mL) and then benzylbromide (8.35 g, 48.83 mmol) and potassium bicarbonate (6.74 g, 48.83 mmol) were added. The mixture was stirred overnight and the organic layer was washed with water. The organic layer was separated, dried over MgSO4 and concentrated. Product was purified from the residue by flash silica gel chromatography to give methyl 4-benzyloxy-3-bromo-5-formyl-benzoate (10.0 g).

Workup

  1. washthe organic layer was washed with water
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customProduct was purified from the residue by flash silica gel chromatography

Sources & evidence

ORD record
ord-bb69740b9d234c069cd5a81612d9ed14
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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