5-Bromosalicylic acid → HCID 67107205, compound

HRID 1623641Notes

Reaction equation

HRID 1623641 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[Br:10][C:11]1[CH:12]=[CH:13][C:14]([OH:20])=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=2)=[C:15]([CH:19]=1)[C:16]([O:18][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=1)=[O:17]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzene

Product 1

HCID 67107205HCID 67107205, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
56 °C

Procedure

3-Chlorobenzyl bromide (568 mg, 2.76 mmol) was added dropwise to a stirred suspension of 5-bromo-2-hydroxybenzoic acid (200 mg, 0.92 mmol) and potassium carbonate (255 mg, 1.84 mmol) in acetone (40 ml) over 1 min. The reaction mixture was stirred at 56° C. for 24 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 an off white solid. 427 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-54230ce2c99a435ab72cf3c1ebc0c3ad
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

Loading…