Thionyl Chloride → 3-Bromo-2-chloro-5-(chloromethyl)pyridine

HRID 1924857Notes

Reaction equation

HRID 1924857 reaction equation
[Cl:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([CH2:9]O)=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>ClCCl>[Cl:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([CH2:9][Cl:13])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20583217(5-BroMo-6-chloropyridin-3-yl)Methanol

Product 1

HCID 249904333-Bromo-2-chloro-5-(chloromethyl)pyridineYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-3-bromo-5-hydroxymethylpyridine (1.0 g, 4.5 mmol) in dichloromethane (20 mL) at 25° C. was added thionyl chloride (361 μL, 4.9 mmol) dropwise. The solution was stirred for 5 h, after which the reaction was quenched with saturated aqueous NaHCO3 and the layers separated. The aqueous phase further extracted with EtOAc (3×) and the combined organic phases dried over MgSO4 and concentrated to furnish 2-chloro-3-bromo-5-chloromethylpyridine as a yellow solid (0.68 g, 63%). GC-MS: Exact mass calcd for C6H5BrCl2N [M+H]+, 241. Found 241.

Workup

  1. customafter which the reaction was quenched with saturated aqueous NaHCO3
  2. customthe layers separated
  3. extractionThe aqueous phase further extracted with EtOAc (3×)
  4. dry with materialthe combined organic phases dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-23e0ce646bf144ea8ed8f41e6017bbec
Source dataset
uspto-grants-2012_05
Patent number
US08178565B2

Reaction notes

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