Water → 5-Bromo-2-(7-bromoheptyloxy)-1,3-dimethylbenzene

HRID 1816725Notes

Reaction equation

HRID 1816725 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][Br:11])=[C:4]([CH3:10])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 169194-Bromo-2,6-dimethylphenolHCID 783091,7-Dibromoheptane

Product 1

HCID 224946365-Bromo-2-(7-bromoheptyloxy)-1,3-dimethylbenzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-2,6-dimethylphenol (2.00 g) and 1,7-dibromoheptane (5.10 g) in N,N-dimethylformamide (20 ml) was treated with potassium carbonate (2.06 g), and the mixture was stirred for 5 hours at ambient temperature. To the reaction mixture was added water and methylene chloride, and the organic layer was separated and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography eluting successively with the following solvents: (1) n-hexane, (2) n-hexane:ethyl acetate=4:1, (3) n-hexane:ethyl acetate=1:1. The fractions containing the object compound were concentrated in vacuo to give crude 5-bromo-2-(7-bromoheptyloxy)-1,3-dimethylbenzene, that was used in the next reaction directly, as a pale yellow oil.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationMagnesium sulfate was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting successively with the following solvents
  7. additionThe fractions containing the object compound
  8. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-7fc2b0d85ff048f1a19a243b72b12415
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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