Water → HCID 66726186, compound

HRID 2284486Notes

Reaction equation

HRID 2284486 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[Br:11].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[CH2:13]([O:10][C:8]1[CH:7]=[CH:6][C:5]([Br:11])=[C:4]([CH:9]=1)[C:3]([O:2][CH3:1])=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 189336882-broMo-5-hydroxybenzoic acid Methyl ester

Product 1

HCID 66726186HCID 66726186, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl-2-bromo-5-hydroxybenzoate (1.0 g, 4.33 mmol), benzyl bromide (0.62 mL, 5.19 mmol), and K2CO3 (780 mg, 5.63 mmol) in anhydrous DMF (8 mL) was stirred at room temperature for 21 h under nitrogen atmosphere. The mixture was poured into equal volumes of water and EtOAc (1:1, 20 mL), then the layers were separated. The aqueous layer was further extracted with equal volume of EtOAc before the organic layers were combined and dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give methyl 5-(benzyloxy)-2-bromobenzoate (1.39 g, 100%).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was further extracted with equal volume of EtOAc before the organic layers
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-b515120c8d584ff092673fa1237aebe5
Source dataset
uspto-grants-2015_09
Patent number
US09145429B2

Reaction notes

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