Benzyl Bromide → Methyl 4-(benzyloxy)-5-bromo-2-hydroxybenzoate

HRID 2373810Notes

Reaction equation

HRID 2373810 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([OH:11])=[CH:6][C:5]=1[OH:12].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([O:11][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:6][C:5]=1[OH:12]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 44828918Methyl 5-bromo-2,4-dihydroxybenzoate

Product 1

HCID 67152890Methyl 4-(benzyloxy)-5-bromo-2-hydroxybenzoateYield 45.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-Bromo-2,4-dihydroxy-benzoic acid methyl ester (1.0 g, 4.04 mmol) in DMF (7 mL) was added Cs2CO3 (1.58 g, 4.85 mmol) and benzylbromide (0.69 g, 4.04 mmol) and heated at 70° C. for 6 h. Reaction mixture was diluted with EtOAc (10 mL) and filtered, filtrate was washed with water, brine and dried over Na2SO4. Solvent was removed under reduced pressure and silicagel column chromatography (EtOAc:Hex, 1:3) gave pure 4-benzyloxy-5-bromo-2-hydroxy-benzoic acid methyl ester (0.62 g).

Workup

  1. customReaction mixture
  2. filtrationfiltered
  3. washfiltrate was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customSolvent was removed under reduced pressure and silicagel column chromatography (EtOAc:Hex, 1:3)

Sources & evidence

ORD record
ord-25cb1447074448cebfe12870d8509f28
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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