Benzyl Bromide → Benzyl 2-benzyloxy-5-chlorobenzoate

HRID 1623667Notes

Reaction equation

HRID 1623667 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:7][C:6]2[CH:10]=[CH:2][CH:3]=[CH:4][CH:5]=2)=[C:6]([CH:10]=1)[C:7]([O:9][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 94475-Chlorosalicylic AcidHCID 11430Potassium Carbonate

Product 1

HCID 13026912Benzyl 2-benzyloxy-5-chlorobenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-chloro-2-hydroxybenzoic acid (2.03 g, 11.8 mmol), benzyl bromide (2.79 ml, 23.5 mmol) and potassium carbonate (4.87 g, 35.3 mmol) in DMF (20 ml) was stirred at room temperature overnight then heated at 60° C. for 1 hour. Cooled, diluted with water (150 ml) and extracted with ethyl acetate (×3). The organics were washed with water (×2) and brine, dried (MgSO4), and concentrated in vacuo to yield the crude title compound as a yellow oil which was used immediately without further purification.

Workup

  1. temperaturethen heated at 60° C. for 1 hour
  2. temperatureCooled
  3. extractionextracted with ethyl acetate (×3)
  4. washThe organics were washed with water (×2) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-420922805c514ca59834e9c618b259c7
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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