5-Bromosalicylic acid → HCID 67107147, compound

HRID 1623653Notes

Reaction equation

HRID 1623653 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[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(=O)([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:10]=[CH:9][CH:8]=[CH:7][C:4]=2[C:5]#[N:6])=[C:16]([CH:20]=1)[C:17]([O:19][CH2:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6])=[O:18]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 67107147HCID 67107147, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

2-(Bromomethyl)benzonitrile (397 mg, 2.027 mmol) was added in one charge 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) 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 (100 ml) and evaporated in vacuo to yield the title compound as an off-white solid. 350 mg.

Workup

  1. customThe organic phase was evaporated
  2. washthe residue was washed with water (25 ml)
  3. extractionextracted with ethyl acetate (100 ml)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-a0acc471208543a693f88462020af60c
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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