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

HRID 1623621Notes

Reaction equation

HRID 1623621 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([OH:17])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH2:13][C:12]2[CH:16]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[C:12]([CH:16]=1)[C:13]([O:15][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:14]

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

Conditions

Temperature
20 °C

Procedure

Solid potassium carbonate (2.76 g, 20 mmol) was added to a solution of 5-bromo-2-hydroxybenzoic acid (1.74 g, 8 mmol) in acetone (20 ml) and the reaction mixture was stirred at 20° C. for 10 mins. (Bromomethyl)benzene (3.42 g, 20 mmol) was added dropwise. The reaction mixture was stirred at 71° C. for 10 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated to give a colourless oil. The crude product was purified on a silica gel column, eluting with hexane:ethyl acetate (100:5) to yield the title compound as a white solid. 3 g.

Workup

  1. stirringThe reaction mixture was stirred at 71° C. for 10 h
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customto give a colourless oil
  6. customThe crude product was purified on a silica gel column
  7. washeluting with hexane:ethyl acetate (100:5)

Sources & evidence

ORD record
ord-d48c62d8054d4036a6188c0b276b2700
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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