Potassium Carbonate → HCID 59596668, compound

HRID 2264828Notes

Reaction equation

HRID 2264828 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 59596668HCID 59596668, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 6-bromo-3-pyridinol (commercial source, 0.870 g, 5.0 mmol) in acetone (20 ml) were added potassium carbonate (1.04 g, 7.5 mmol) and 1-(bromomethyl)-2-fluorobenzene (Aldrich, 1.2 ml, 10.0 mmol) and the mixture was stirred for three hours at r.t. The solvent was evaporated and the residue was diluted with water and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel using cyclohexane/ethyl acetate (1:0 to 98:2) to afford the title compound as a white solid (1.28 g, 90%). MS: (ES/+) m/z: 282, 284 [MH]+ C12H9BrFNO requires 281, 283; 1H NMR (400 MHz, CDCl3) δ (ppm): 8.12-8.20 (m, 1H); 7.43-7.53 (m, 1H); 7.32-7.43 (m, 2H); 7.16-7.24 (m, 2H); 7.07-7.16 (m, 1H); 5.17 (s, 2H).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2c7face95148406088e88024c1c8e6a9
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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