Thionyl Chloride → 5-Bromo-4-isopropoxy-3-methyl-2-chloromethyl-1-benzofuran

HRID 29476Notes

Reaction equation

HRID 29476 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10]O)=[C:7]([CH3:12])[C:6]=2[C:13]=1[O:14][CH:15]([CH3:17])[CH3:16].S(Cl)([Cl:20])=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][Cl:20])=[C:7]([CH3:12])[C:6]=2[C:13]=1[O:14][CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68714044(5-Bromo-4-isopropoxy-3-methyl-1-benzofuran-2-yl)methanol

Product 1

HCID 687156825-Bromo-4-isopropoxy-3-methyl-2-chloromethyl-1-benzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-4-isopropoxy-3-methyl-1-benzofuran-2-yl) methanol (0.3 g, 1 mmole) in 10 mL dichloromethane was added 0.73 mL of thionyl chloride and the reaction was stirred at room temperature for 2 hours. The solvent was concentrated in vacuo, the residue was added toluene to provide 0.33 g of 5-bromo-4-isopropoxy-3-methyl-2-chloromethyl-1-benzofuran.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. additionthe residue was added toluene

Sources & evidence

ORD record
ord-f6afb000054b4925a3dcdffdda2dd3fe
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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