5-Bromosalicylic acid → HCID 67107475, compound

HRID 1623721Notes

Reaction equation

HRID 1623721 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])=[C:6]([CH:10]=1)[C:7]([O:9][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27])=[O:8]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzene

Product 1

HCID 67107475HCID 67107475, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-bromo-2-hydroxybenzoic acid (2.5 g, 11.52 mmol) in acetone (100 ml) was added potassium carbonate (3.98 g, 28.8 mmol) and 1-(bromomethyl)-2,4-difluorobenzene (3.25 ml, 25.3 mmol). The mixture was heated to reflux for 4 hours. On cooling the mixture was filtered to remove the carbonate, the solid was washed with acetone (50 ml). The organics were evaporated under reduced pressure to give a white solid 5.39 g. No attempt was made to purify this compound it was taken on as is.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureOn cooling the mixture
  4. filtrationwas filtered
  5. customto remove the carbonate
  6. washthe solid was washed with acetone (50 ml)
  7. customThe organics were evaporated under reduced pressure

Sources & evidence

ORD record
ord-eab6251d6c09434b8b2f638328804a4b
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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