5-Bromosalicylic acid → HCID 67106970, compound

HRID 1623651Notes

Reaction equation

HRID 1623651 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[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-].[Cs+].[Cs+]>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]=[CH:5][C:4]=2[O:25][CH3:22])=[C:16]([CH:20]=1)[C:17]([O:19][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10])=[O:18]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 10796Cesium carbonateHCID 814952-(Chloromethyl)anisole

Product 1

HCID 67106970HCID 67106970, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

Neat 1-(chloromethyl)-2-methoxybenzene (397 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 cesium carbonate (751 mg, 2.30 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 with ethyl acetate (3×30 ml) and evaporated in vacuo to yield the title compound as a light yellow liquid. 420 mg.

Workup

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

Sources & evidence

ORD record
ord-78515ee9aae54b1c9a6e0eeb2a21f507
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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