Ethanol → 3-Bromo-5-phenylpyridine

HRID 1654640Notes

Reaction equation

HRID 1654640 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 693693,5-Dibromopyridine

Product 1

HCID 27629043-Bromo-5-phenylpyridineYield 28%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Tetrakis(triphenylphosphine)palladium (577 mg; 0.5 mM) was added to 3,5-dibromopyridine (5.214 g; 22 mM) in 40 mL of toluene at R.T. under nitrogen. After 10 minutes stirring, 25 mL of 2M aqueous sodium carbonate solution, phenylboronic acid (2.44 g; 20 mM), and 10 mL of ethanol were added, and the mixture was heated 11 hours at 80° C. The reaction mixture was cooled, diluted with 75 mL of ethyl acetate and washed with 2×15 mL of saturated sodium carbonate solution, and then dried over anhydrous magnesium sulfate. Solvent removal gave crude product, which was chromatographed on silica gel using ethyl acetate:hexane (1:5) mixture to give a white solid boiling at 100°-101° C./~0.1 mm in 28% yield.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with 2×15 mL of saturated sodium carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customSolvent removal
  5. customgave crude product, which
  6. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-990a67fdb41b4981a82e1f75e2f55256
Source dataset
uspto-grants-1995_04
Patent number
US05409920

Reaction notes

Loading…