Potassium Carbonate → HCID 118075930, compound

HRID 1051577Notes

Reaction equation

HRID 1051577 reaction equation
Br[CH:2]1[CH2:5][CH2:4][CH2:3]1.[F:6][C:7]1[C:15]([F:16])=[CH:14][C:13]([OH:17])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:2]1([O:17][C:13]2[CH:14]=[C:15]([F:16])[C:7]([F:6])=[C:8]([CH:12]=2)[C:9]([O:11][CH:2]2[CH2:5][CH2:4][CH2:3]2)=[O:10])[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78110BromocyclobutaneHCID 265967652,3-Difluoro-5-hydroxybenzoic acid

Product 1

HCID 118075930HCID 118075930, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Bromocyclobutane (150 g, 1.12 mol) was added to a mixture of 2,3-difluoro-5-hydroxybenzoic acid (50 g, 287 mmol), and potassium carbonate (230 g, 1.67 mol) in acetonitrile (1500 mL), and the resulting mixture stirred overnight at 90° C. The reaction mixture was cooled to room temperature, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with petroleum ether) to afford cyclobutyl 5-cyclobutoxy-2,3-difluorobenzoate (49 g, 60%) as a yellow green solid. MS (ESI, pos. ion) m/z 283 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified via column chromatography on silica gel (eluting with petroleum ether)

Sources & evidence

ORD record
ord-264ac456013f4fb2a20f58ef5b2936a5
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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