Thionyl Chloride → 1-Bromo-2-(chloromethyl)-4,5-dimethoxybenzene

HRID 604166Notes

Reaction equation

HRID 604166 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12]O.S(Cl)([Cl:16])=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][Cl:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 618887(2-Bromo-4,5-dimethoxyphenyl)methanol

Product 1

HCID 49622811-Bromo-2-(chloromethyl)-4,5-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Bromo-4,5-dimethoxy-phenyl)-methanol (2.47 g) is dissolved in methylene chloride (30 ml) and thereto is added thionyl chloride (875 μl), and the mixture is stirred at room temperature for 30 minutes. The reaction solution is concentrated under reduced pressure, and thereto is added hexane and the resulting crystal is filtered to give 1-bromo-2-chloromethyl-4,5-dimethoxy-benzene (2.25 g). MS (m/z): 229/231

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionis added hexane
  3. filtrationthe resulting crystal is filtered

Sources & evidence

ORD record
ord-7d6b77474a7641058318025df334334e
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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