1,2-Dimethoxyethane → 2-Chloro-4-phenylpyridine

HRID 1844935Notes

Reaction equation

HRID 1844935 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>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.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 15165112-Chloro-4-iodopyridine

Product 1

HCID 27628422-Chloro-4-phenylpyridineYield 82%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-chloro-4-iodopyridine (20.0 g, 82 mmol), phenylboronic acid (10.2 g, 82 mmol), Pd(Ph3P)4 (2.84 g 2.46 mmol), sodium carbonate (26.0 g, 246 mmol), DME (600 mL) and water (150 mL) was degassed with nitrogen and then refluxed overnight. The reaction was concentrated and the extracted with ethyl acetate. The ethyl acetate layer was dried on Na2SO4 and then vacuum distilled to give 2-chloro-4-phenylpyridine (2.79 g. 12.7 mmol. 82% yield).

Workup

  1. customwas degassed with nitrogen
  2. temperaturerefluxed overnight
  3. concentrationThe reaction was concentrated
  4. extractionthe extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried on Na2SO4
  6. distillationvacuum distilled

Sources & evidence

ORD record
ord-dface043aeac48339c33048ebe5a94dc
Source dataset
uspto-grants-2015_02
Patent number
US08946697B1

Reaction notes

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