Thionyl Chloride → 3-Bromo-4-(chloromethyl)pyridine

HRID 2207143Notes

Reaction equation

HRID 2207143 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8]O.S(Cl)([Cl:12])=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][Cl:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 46840038(3-Bromopyridin-4-yl)methanol

Product 1

HCID 669333093-Bromo-4-(chloromethyl)pyridineYield 118.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-4-(hydroxymethyl)pyridine (1.6 g, 8.4 mmol) in methylene chloride (90 mL) was added thionyl dichloride (1.6 mL, 22.0 mmol) dropwise over at 0° C. The reaction was stirred at room temperature for 2 h and then concentrated. The yellow solid was dried in a vacuum to afford the compound 5 (2.05 g, 100%).

Workup

  1. concentrationconcentrated
  2. customThe yellow solid was dried in a vacuum

Sources & evidence

ORD record
ord-34289a9d3a81428eb86bfa29c3d4b45d
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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