2-Bromopyridine → 2-(3-Bromophenyl)pyridine

HRID 45436Notes

Reaction equation

HRID 45436 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1.C(COC)OC.C(=O)([O-])[O-].[K+].[K+]>O.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:9]1[CH:14]=[C:13]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 79732-BromopyridineHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2734318(3-Bromophenyl)boronic acid

Product 1

HCID 111155062-(3-Bromophenyl)pyridineYield 75%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-bromopyridine (4.8 g, 30.33 mmol), 3-bromophenyl boronic acid (4.06 g, 20.22 mmol), glyme (35 mL), tetrakis(triphenylphosphine)palladium(0) (0.4 g) and a solution of potassium carbonate (7.6 g, 55 mmol) in water (35 mL) was stirred well at reflux under nitrogen overnight. After cooling, the reaction mixture was diluted with ethyl acetate (600 mL) and washed with water (3×200 mL). The solvent and excess 2-bromopyridine were removed on a rotary evaporator (bath temperature=75° C.) and the crude product was purified by chromatography on silica (110 g) with 2% ethyl acetate in heptane (6 L) to produce 1 (3.55 g, 75%).

Workup

  1. temperatureat reflux under nitrogen overnight
  2. temperatureAfter cooling
  3. washwashed with water (3×200 mL)
  4. customThe solvent and excess 2-bromopyridine were removed on a rotary evaporator (bath temperature=75° C.)
  5. customthe crude product was purified by chromatography on silica (110 g) with 2% ethyl acetate in heptane (6 L)

Sources & evidence

ORD record
ord-7c1a895424ee4f9aa5b900cf7094252a
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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