5-Bromosalicylic acid → Benzyl 2-(benzyloxy)-5-bromobenzoate

HRID 1623622Notes

Reaction equation

HRID 1623622 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:9][C:10]1[CH:11]=[CH:12][C:13]([OH:19])=[C:14]([CH:18]=1)[C:15]([OH:17])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[C:14]([CH:18]=1)[C:15]([O:17][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:16]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Neat (bromomethyl)benzene (17.10 g, 100 mmol) was added to a stirred suspension of 5-bromo-2-hydroxybenzoic acid (8.68 g, 40.0 mmol) and potassium carbonate (13.82 g, 100 mmol) in acetone (150 ml) at 20° C. over 1 min. The reaction mixture was refluxed overnight. After filtration, the filtrate was evaporated to yield the title compound as an oil which was used in the next step without further purification. 15 g.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationAfter filtration
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-d613d9520afd4a8c88d8692ad46c142b
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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