5-Bromosalicylic acid → HCID 67106781, compound

HRID 1623703Notes

Reaction equation

HRID 1623703 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([OH:17])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1>CC(C)=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[C:12]([CH:16]=1)[C:13]([O:15][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)=[O:14]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromide

Product 1

HCID 67106781HCID 67106781, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

Solid potassium carbonate (2.76 g, 20 mmol) was added to a stirred solution of 5-bromo-2-hydroxybenzoic acid (1 g, 4.61 mmol) in acetone (20 ml) at 20° C. The reaction mixture was stirred at 20° C. for 10 min, and then 1-(bromomethyl)-3-fluorobenzene (1.92 g, 10.14 mmol) was added dropwise. The reaction mixture was stirred at 71° C. for 18 h. After cooling to room temperature, the mixture was filtered. The filtrate was concentrated to give a colourless oil. The crude product was added to a silica gel column and was eluted with hexane/ethyl acetate (100:5 then 20:1) to yield the title compound as a white solid. 1.65 g.

Workup

  1. stirringThe reaction mixture was stirred at 71° C. for 18 h
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated
  5. customto give a colourless oil
  6. washwas eluted with hexane/ethyl acetate (100:5

Sources & evidence

ORD record
ord-0ce6d3fdf88344328f48834aa0424ce4
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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