Thionyl Chloride → 1-[(4-Bromophenyl)chloromethyl]-3-methoxybenzene

HRID 893289Notes

Reaction equation

HRID 893289 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)O)=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([Cl:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18507125HCID 18507125, compound

Product 1

HCID 189559361-[(4-Bromophenyl)chloromethyl]-3-methoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude alcohol from above (6.5 g, 22 mmole) was dissolved in 50 ml of dichloromethane, and 2.4 ml (33 mmole) of thionyl chloride was added dropwise at room temperature. The reaction was allowed to stir overnight and the solvent was removed under vacuum. The crude product was redissolved in 50 ml of toluene and the solvent was again removed under vacuum in order to eliminate excess thionyl chloride, providing 6.85 g of crude 4-bromo-3'-methoxybenzhydryl chloride as a dark oil.

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionThe crude product was redissolved in 50 ml of toluene
  3. customthe solvent was again removed under vacuum in order

Sources & evidence

ORD record
ord-c3688242e5cb4b27a3ab26a15a04bae7
Source dataset
uspto-grants-1992_06
Patent number
US05124330

Reaction notes

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