Thionyl Chloride → 4-Bromo-2-(chloromethyl)-1-iodobenzene

HRID 594819Notes

Reaction equation

HRID 594819 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH2:8]O)[CH:7]=1.O=S(Cl)[Cl:13]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH2:8][Cl:13])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15339730(5-Bromo-2-iodophenyl)methanol

Product 1

HCID 706632554-Bromo-2-(chloromethyl)-1-iodobenzeneYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-2-iodophenyl)methanol (1.4 g, 4.5 mmol) in DCM (20 mL) was added SOCl2 (3.2 g, 26.9 mmol) at 0° C., and the reaction was stirred at rt overnight. The solution was concentrated, and the residue was purified silica gel chromatography (PE) to give 1.2 g (81%) of the title compound as a brown solid.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified silica gel chromatography (PE)

Sources & evidence

ORD record
ord-98b05e593d384d7abb8601619ed51ee2
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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