Benzyl Bromide → HCID 40567378, compound

HRID 646523Notes

Reaction equation

HRID 646523 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-9f2ca791156e48c19f1e472304ed412a
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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