Sodium Carbonate → 3,5-Dichloro-4-(chloromethyl)pyridine

HRID 1959543Notes

Reaction equation

HRID 1959543 reaction equation
O=S(Cl)[Cl:3].[Cl:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([Cl:14])[C:11]=1[CH2:12]O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([Cl:14])[C:11]=1[CH2:12][Cl:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 17855219(3,5-Dichloropyridin-4-yl)methanol

Product 1

HCID 226268533,5-Dichloro-4-(chloromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

SOCl2 (2.3 mL, 32 mmol) was added dropwise to a stirred solution of (3,5-dichloropyridin-4-yl)-methanol (2.83 g, 15.9 mmol) in DCM (20 mL) over 10 min. After stirring for 35 min at room temperature, saturated aqueous Na2CO3 solution (40 mL) and DCM (60 mL) was added to the reaction mixture. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with EA/hexane 1:4) to give the title compound. MS (m/z): 196.0 [M+H+].

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel (elution with EA/hexane 1:4)

Sources & evidence

ORD record
ord-982022f530b7442885a8c66a98fb0b0e
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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