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

HRID 2036821Notes

Reaction equation

HRID 2036821 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][Cl:12])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 117012593-Bromo-5-(chloromethyl)pyridineYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-pyridin-3-yl)-methanol (0.5 g, 2.68 mmol) in DCM (10 mL) was added thionyl chloride (0.5 mL). The resulting solution was stirred at room temperature for 2 h. After this time, the reaction mixture was quenched with water and extracted into DCM. The organic extracts were washed with brine filtered and concentrated under reduced pressure to give 3-bromo-5-chloromethyl-pyridine (0.45 g, 82%), which was used in the next step without further purification.

Workup

  1. customAfter this time, the reaction mixture was quenched with water
  2. extractionextracted into DCM
  3. washThe organic extracts were washed with brine
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6bb5e36dd866430c8a8e771600154235
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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