Chlorine → HCID 14986395, compound

HRID 1613074Notes

Reaction equation

HRID 1613074 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=1[O:15][CH3:16].[Cl:17]Cl>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[C:12]([Cl:17])=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 14986394HCID 14986394, compound

Product 1

HCID 14986395HCID 14986395, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4.0 g of 1-(5-bromopentyl)-2,3-dimethoxybenzene in 50 mL of methylene chloride cooled in an ice bath was added 18 mL of 0.8M chlorine in methylene chloride. 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 2.60 g (58% yield) of 1-(5-bromopentyl)-6-chloro-2,3-dimethoxybenzene. The nmr spectrum was consistent with the structure and the mass spectrum gave a molecular ion at m/z 320 (C13H18BrClO2).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto yield an oil
  3. customPurification by HPLC

Sources & evidence

ORD record
ord-5d67db2c30ce45f984f9d76b2038a823
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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