5-Bromosalicylic acid → HCID 67107679, compound

HRID 1623649Notes

Reaction equation

HRID 1623649 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[Br:11][C:12]1[CH:13]=[CH:14][C:15]([OH:21])=[C:16]([CH:20]=1)[C:17]([OH:19])=[O:18].[C:22](=[O:25])([O-])[O-].[K+].[K+]>CC(C)=O>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([O:25][CH3:22])[CH:4]=2)=[C:16]([CH:20]=1)[C:17]([O:19][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1)=[O:18]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 40672073-Methoxybenzyl bromide

Product 1

HCID 67107679HCID 67107679, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

Neat 1-(bromomethyl)-3-methoxybenzene (510 mg, 2.53 mmol) was added in one charge to a stirred suspension of 5-bromo-2-hydroxybenzoic acid (250 mg, 1.15 mmol) and potassium carbonate (318 mg, 2.304 mmol) in acetone (40 ml) under nitrogen at 20° C. The reaction mixture was stirred at 55° C. for 16 h. The organic phase was evaporated and the residue was washed with water (25 ml), extracted by ethyl acetate (3×30 ml) and evaporated in vacuo to yield the title compound as an off-white solid. 430 mg.

Workup

  1. customThe organic phase was evaporated
  2. washthe residue was washed with water (25 ml)
  3. extractionextracted by ethyl acetate (3×30 ml)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-34b0e1e372d74ca9bb5d456e5715a221
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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