5-Bromosalicylic acid → HCID 67106784, compound

HRID 1623711Notes

Reaction equation

HRID 1623711 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])=[C:22]([F:27])[CH:21]=1>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])=[C:22]([F:27])[CH:21]=2)=[C:6]([CH:10]=1)[C:7]([O:9][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=1)=[O:8]

Participants

5

Reactant 3

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 5814364-(Bromomethyl)-1,2-difluorobenzene

Product 1

HCID 67106784HCID 67106784, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 5-bromo-2-hydroxybenzoic acid (1.8 g, 8.29 mmol) in acetone (50 ml) at room temperature was added potassium carbonate (2.87 g, 20.74 mmol) followed by 4-(bromomethyl)-1,2-difluorobenzene (2.34 ml, 18.25 mmol). The mixture was stirred at room temperature for 30 min and then heated to reflux for 15 hr. The solid was filtered off and washed with acetone (3×50 ml). The organic layer was evaporated under reduced pressure and the oil was purified by chromatography using a silica cartridge, eluting with 0-15% ethyl acetate/isohexane to give a clear oil, which solidified on standing to yield the title compound. 3.9 g.

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 hr
  3. filtrationThe solid was filtered off
  4. washwashed with acetone (3×50 ml)
  5. customThe organic layer was evaporated under reduced pressure
  6. customthe oil was purified by chromatography
  7. washeluting with 0-15% ethyl acetate/isohexane
  8. customto give a clear oil, which

Sources & evidence

ORD record
ord-91c6008f59124614ba125bb14f03bd7d
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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