Thionyl Chloride → 5-(Chloromethyl)-2-phenylpyridine

HRID 349962Notes

Reaction equation

HRID 349962 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([C:11]2[N:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:3][CH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 22254216(6-Phenylpyridin-3-yl)methanol

Product 1

HCID 27638625-(Chloromethyl)-2-phenylpyridineYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Thionyl chloride (10 ml) was slowly added to a solution of 6-phenyl-3-pyridylmethanol (11.60 g) in toluene (100 ml) at room temperature, which was stirred at 100° C. for 1 hour. After cooling, the reaction mixture was poured into saturated aqueous sodium bicarbonate solution, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated to obtain 5-chloromethyl-2-phenylpyridine (11.49 g, yield 89%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 95–96° C.

Workup

  1. temperatureAfter cooling
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0d4cbb3c57be402f9753ac6ddd4e16a2
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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