3-Bromo-2-ethoxypyridine → 5,5'-Bis[2-ethoxypyridine]

HRID 404526

Reaction equation

HRID 404526 reaction equation
Br[C:2]1[C:3]([O:8][CH2:9][CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=1>[N+](CC)(CC)(CC)CC.[I-].C1COCC1.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Zn]>[CH2:9]([O:8][C:3]1[N:4]=[CH:5][C:6]([C:6]2[CH:5]=[N:4][C:3]([O:8][CH2:9][CH3:10])=[CH:2][CH:7]=2)=[CH:7][CH:2]=1)[CH3:10]

Participants

6

Reactant 1

HCID 109873083-Bromo-2-ethoxypyridine

Product 1

HCID 8247525,5'-Bis[2-ethoxypyridine]

Reagents, catalysts & solvents 4

HCID 6225Tetraethylammonium IodideCatalystHCID 23994ZincCatalystHCID 178418751HCID 178418751, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared as described by Constable et al.13 using NiCl2(PPh3)2 (327 mg, 0.5 mmol, 0.3 eq.), acid washed Zn powder (164 mg, 1.5 eq.) and Et4NI (435 mg, 1.7 mmol, 1 eq.) in. distilled THF (10 mL). with a solution of 5 bromo-2 ethoxypyridine (344 mg, 1.7 mmol, 1 eq.) in THF (5 mL) at 50° C. for 24 h. Workup gave a white crystalline solid (237 mg; 80%). The reaction was also carried out on a larger scale (1.0 g or 1.7 g of starting material) giving yields of 85% and 90% respectively. The spectral data were consistent with literature data13.

Workup

  1. customWorkup gave a white crystalline solid (237 mg; 80%)
  2. customgiving
  3. customyields of 85% and 90% respectively

Sources & evidence

ORD record
ord-ff3335dd637e438d845ea43517055040
Source dataset
uspto-grants-2014_06
Patent number
US08748582B2

Linked notes

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