Thionyl Chloride → 5-Bromo-2-(3-(chloromethyl)phenyl)pyrimidine

HRID 474208Notes

Reaction equation

HRID 474208 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH2:14]O)[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1.S(Cl)([Cl:18])=O>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][Cl:18])[CH:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59484879(3-(5-Bromopyrimidin-2-yl)phenyl)methanol

Product 1

HCID 594380475-Bromo-2-(3-(chloromethyl)phenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

80 g (302 mmol) of [3-(5-bromopyrimidin-2-yl)phenyl]methanol are suspended in 300 ml of dichloromethane, and 33 ml (453 mmol) of thionyl chloride are slowly added with cooling. The reaction mixture is stirred at room temperature for 3 h. The solvent was distilled off, co-evaporated 3 times with toluene and stirred with diethyl ether:

Workup

  1. temperaturewith cooling
  2. distillationThe solvent was distilled off
  3. stirringco-evaporated 3 times with toluene and stirred with diethyl ether

Sources & evidence

ORD record
ord-dccdc4d472954f8aa9071115cb2aeeed
Source dataset
uspto-grants-2014_01
Patent number
US08637518B2

Reaction notes

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