Pyridine → 1-Bromo-3-chloromethyl-2,5-dimethoxy-benzene

HRID 2393581Notes

Reaction equation

HRID 2393581 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5]O.N1C=CC=CC=1.S(Cl)([Cl:22])=O>CCOCC>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5][Cl:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 101927773-Bromo-2,5-dimethoxybenzyl Alcohol

Product 1

HCID 103081541-Bromo-3-chloromethyl-2,5-dimethoxy-benzeneYield 86.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 8.18 gm (33.11 mmol) of 3-bromo-2,5-dimethoxybenzyl alcohol and 0.8 ml pyridine in 100 ml ether was added dropwise a solution of 8.5 ml (116 mmol) thionyl chloride in 20 ml ether. After stirring at ambient temperature for 20 hours, the reaction mixture was poured onto ice. The ether extract was washed with brine, dried (NaSO4), filtered and concentrated in vacuo to give 7.59 gm of a colorless oil. A portion, 3.9 gm, was purified by silica gel chromatography using 3:7 CH2 Cl2 :hexane to yield 3.62 gm of a white solid.

Workup

  1. additionthe reaction mixture was poured onto ice
  2. extractionThe ether extract
  3. washwas washed with brine
  4. dry with materialdried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62cfc9a089764bcdb5a83111f341356a
Source dataset
uspto-grants-1998_09
Patent number
US05807897

Reaction notes

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