Benzyl Bromide → HCID 40567378, compound

HRID 2097309Notes

Reaction equation

HRID 2097309 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:13]([O-:16])([O-])=O.[K+].[K+].C(Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[C:13]([O:12][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Product 1

HCID 40567378HCID 40567378, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 5-chloro-2-hydroxy-benzoate (2.5 g, 13.4 mmol), K2CO3 (3.7 g, 26.8 mmol) and benzyl bromide (2.98 g, 17.4 mmol) in acetone (30 ml) was refluxed for 12 hours. After cooling, acetone was evaporated. EtOAc (100 ml) was added and filtered. The organic layer was then washed with 1M HCl (1×80 ml), brine (2×80 ml) and dried with Na2SO4. After filtration and evaporation of the solvent, yellow semi-solids were obtained (3.2 g). 1H NMR (d6-acetone) δ=7.73 (1H, d); 7.60-7.30 (1H+5H, m); 7.28 (1H, d); 5.30 (2H, s) and 3.90 (3H, s).

Workup

  1. temperaturewas refluxed for 12 hours
  2. temperatureAfter cooling
  3. customacetone was evaporated
  4. additionEtOAc (100 ml) was added
  5. filtrationfiltered
  6. washThe organic layer was then washed with 1M HCl (1×80 ml), brine (2×80 ml)
  7. dry with materialdried with Na2SO4
  8. filtrationAfter filtration and evaporation of the solvent
  9. customyellow semi-solids were obtained (3.2 g)

Sources & evidence

ORD record
ord-1cbd620df33f4e6caa9ac601e3caef56
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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