Dichloromethane → HCID 14986396, compound

HRID 1613075Notes

Reaction equation

HRID 1613075 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=C[CH:10]=[C:9]([O:13][CH3:14])[C:8]=1[O:15][CH3:16].[Cl:17]Cl.[CH2:19]([Cl:21])Cl>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[C:12]([Cl:17])=[C:19]([Cl:21])[CH:10]=[C:9]([O:13][CH3:14])[C:8]=1[O:15][CH3:16]

Participants

4

Reactant 3

HCID 6344Dichloromethane3×HCID 24526Chlorine2×HCID 14986394HCID 14986394, compound

Product 1

HCID 14986396HCID 14986396, compoundYield 41%

Procedure

To 4.0 g of 1-(5-bromopentyl)-2,3-dimethoxy benzene in 50 mL of methylene chloride cooled in an ice bath was added 18 mL of 0.8M chlorine in methylene chloride. After 15 minutes, 17 mL of 0.88M chlorine in methylene chloride was added. The reaction mixture was kept at 0° for 3 hours and then was concentrated under reduced pressure to yield an oil. Purification by HPLC using 30% toluene-hexane gave 2.03 g (41% yield) of 1-(5-bromopentyl)-5,6-dichloro-2,3-dimethoxybenzene. The nmr spectrum was consistent with the structure and the mass spectrum gave a molecular ion at m/z 354 (C13H17BrCl2O2).

Workup

  1. waitThe reaction mixture was kept at 0° for 3 hours
  2. concentrationwas concentrated under reduced pressure
  3. customto yield an oil
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-1bcfbb032fc9461b8e60ac1ad2bd3b8e
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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