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

HRID 1521583Notes

Reaction equation

HRID 1521583 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>ClCCl>[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)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of (5-bromopyridin-3-yl)methanol (38.8 g, 0.206 mol) in dichloromethane (0.6 L) was added a solution of thionyl chloride (149 mL, 2.05 mol) in dichloromethane (200 mL). The resulting mixture was stirred at reflux overnight. The reaction was then concentrated under reduced pressure, and the resulting residue was recrystallized from diethyl ether to provide the title compound: LCMS m/z 206 [M+H]+; 1H NMR (300 MHz, d6-DMSO) δ 12.66 (s, 1H), 8.69-8.74 (m, 2H), 8.25 (s, 1H), 4.83 (s, 2H).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction was then concentrated under reduced pressure
  3. customthe resulting residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-337dfeb0a5a04e36ae17d3b12539f65f
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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