Potassium Carbonate → 4-Bromo-2-chloro-1-(octyloxy)benzene

HRID 898190Notes

Reaction equation

HRID 898190 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:4]([Cl:9])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123801-IodooctaneHCID 198594-Bromo-2-chlorophenol

Product 1

HCID 688111074-Bromo-2-chloro-1-(octyloxy)benzeneYield 77.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Bromo-3-chloro-4-hydroxybenzene (0.50 g, 2.41 mmol) was dissolved in acetonitrile (20 mL) and stirred at rt. Potassium carbonate (0.47 g, 3.37 mmol) and iodooctane (0.57 mL, 3.13 mmol) were added and the reaction was heated to 80° C. for 4 h. The reaction was diluted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. Silica gel chromatography eluting with 1% ethyl acetate/hexane yielded 0.6 g of product: ESI-MS 317.0 (M+H).

Workup

  1. temperaturethe reaction was heated to 80° C. for 4 h
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washSilica gel chromatography eluting with 1% ethyl acetate/hexane

Sources & evidence

ORD record
ord-610740129f2a479f8e588624b9fe5854
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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