Thionyl Chloride → 2-(3-(Chloromethyl)phenoxy)-5-methylpyridine

HRID 1666403Notes

Reaction equation

HRID 1666403 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH2:15]O)[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.S(Cl)([Cl:19])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:19][CH2:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66875995(3-(5-Methylpyridin-2-yloxy)phenyl)methanol

Product 1

HCID 668767842-(3-(Chloromethyl)phenoxy)-5-methylpyridineYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-(5-Methylpyridin-2-yloxy)phenyl)methanol from Step 1 (1.9 g, 8.8 mmol), in dichloromethane (25 mL), was cooled to 0° C., and treated dropwise with thionyl chloride (0.773 mL, 10.6 mmol). The reaction mixture was allowed to warm to ambient temperature and was stirred for 3 h. Saturated aqueous sodium bicarbonate (20 mL) was added and the mixture was stirred at RT for 5 min. The organic layer was separated, dried over sodium sulfate, filtered and concentrated by evaporation to afford the title compound (2.1 g, 99% yield) as an oil.

Workup

  1. stirringthe mixture was stirred at RT for 5 min
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4544dc8335674961b2784c4136e41739
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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