Sodium Carbonate → 6-(4-Pentylphenyl)-1-chloro-2-naphthol

HRID 645315Notes

Reaction equation

HRID 645315 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:12])=[C:7]([OH:13])[CH:6]=[CH:5]2.[CH2:14]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)[CH2:15][CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C(O)C>[CH2:14]([C:19]1[CH:20]=[CH:21][C:22]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([Cl:12])=[C:7]([OH:13])[CH:6]=[CH:5]3)=[CH:23][CH:24]=1)[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 4589191(4-Pentylphenyl)boronic acidHCID 220481596-Bromo-1-chloronaphthalen-2-ol

Product 1

HCID 592642786-(4-Pentylphenyl)-1-chloro-2-naphtholYield 72.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

55 g of 6-bromo-1-chloro-2-naphthol (S1-2), 12.3 g of 4-pentylphenylboronic acid (S1-3), 1.0 g of tetrakistriphenylphosphine palladium, 13.6 g of sodium carbonate and 100 mL of a mixed solvent of toluene, ethanol and water (3/3/1) were added to a reactor under a nitrogen atmosphere and refluxed for 10 hours. The reaction mixture was cooled to room temperature, and toluene was added thereto. The reaction mixture was washed with 1N hydrochloric acid and water, and after drying over magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography with toluene as a developing solvent to provide 15 g of 6-(4-pentylphenyl)-1-chloro-2-naphthol (S1-4).

Workup

  1. temperaturerefluxed for 10 hours
  2. washThe reaction mixture was washed with 1N hydrochloric acid and water
  3. dry with materialafter drying over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography with toluene as a developing solvent

Sources & evidence

ORD record
ord-a7d5cbae512148789854524e8b8422ca
Source dataset
uspto-grants-2010_04
Patent number
US07704409B2

Reaction notes

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