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

HRID 1623623Notes

Reaction equation

HRID 1623623 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

Conditions

Temperature
70 °C

Procedure

(Bromomethyl)benzene (34.2 ml, 288 mmol) was added over 5 minutes to a stirred suspension of 5-bromo-2-hydroxybenzoic acid (28.4 g, 131 mmol) and potassium carbonate (45.2 g, 327 mmol) in acetone (300 ml) in air at room temperature. The reaction mixture was stirred at 70° C. overnight. After filtering, the filtrate was evaporated to give a light yellow oil, dried in a vacuum to give yellow solid, which was washed by petroleum ether (300 ml×2), filtered and dried in vacuum to yield the title compound as a white solid. 48.2 g.

Workup

  1. filtrationAfter filtering
  2. customthe filtrate was evaporated
  3. customto give a light yellow oil
  4. customdried in a vacuum
  5. customto give yellow solid, which
  6. washwas washed by petroleum ether (300 ml×2)
  7. filtrationfiltered
  8. customdried in vacuum

Sources & evidence

ORD record
ord-6429c0d3bcca474fb681ab40febefc17
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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