Benzyl Bromide → Methyl 2-(benzyloxy)-3-formylbenzoate

HRID 1529538Notes

Reaction equation

HRID 1529538 reaction equation
[CH:1]([C:3]1[C:4]([OH:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.CCOC(C)=O.O>[CH2:20]([O:13][C:4]1[C:3]([CH:1]=[O:2])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 345559Methyl 3-formyl-2-hydroxybenzoate

Product 1

HCID 86720697Methyl 2-(benzyloxy)-3-formylbenzoateYield 62.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of methyl 3-formyl-2-hydroxybenzoate (640 mg, 3.56 mmol), K2CO3 (982 mg, 7.12 mmol) and benzyl bromide (0.63 mL, 5.34 mmol) in DMF (3 mL) was stirred at room temperature for 16 hours and diluted with EtOAc (100 mL) and water (40 mL). The layers were separated and the organic phase dried over MgSO4. After filtration and concentration in vacuo, the residue was purified via silica gel chromatography, eluting with 0-15% EtOAc in isohexane, to give the title compound as a white solid (598 mg, 62%).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic phase dried over MgSO4
  3. filtrationAfter filtration and concentration in vacuo
  4. customthe residue was purified via silica gel chromatography
  5. washeluting with 0-15% EtOAc in isohexane

Sources & evidence

ORD record
ord-774f45fdf6e0477ab71a55ad7014d50d
Source dataset
uspto-grants-2015_07
Patent number
US09090606B2

Reaction notes

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