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

HRID 11989Notes

Reaction equation

HRID 11989 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](OB(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.C(O)C.O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[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 4

HCID 10340Sodium CarbonateHCID 220481596-Bromo-1-chloronaphthalen-2-olHCID 234509174-Pentylphenylboric acidHCID 86587398Ethanol toluene water

Product 1

HCID 592642786-(4-Pentylphenyl)-1-chloro-2-naphtholYield 78.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

At first, 55 g of 6-bromo-1-chloro-2-naphthol (S1-2), 12.3 g of 4-pentyl-phenylboric acid (S1-3), 1.0 g of tetrakis(triphenylphosphine) palladium, 13.6 g of sodium carbonate and 100 ml of a mixed solvent of toluene/ethanol/water=3/3/1 were added to a reactor in nitrogen atmosphere and refluxed for 10 hours. The reaction solution was cooled to room temperature, added with toluene, and then washed with 1N HCl(aq) and water, dried over magnesium sulfate and distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using toluene as an eluting solvent, and then dried under a reduced pressure to obtain 15 g of 6-(4-pentylphenyl)-1-chloro-2-naphthol (S1-4).

Workup

  1. temperaturerefluxed for 10 hours
  2. washwashed with 1N HCl(aq) and water
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled under a reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-ecfb716693ae4e1b944330ff514b9b38
Source dataset
uspto-grants-2010_06
Patent number
US07727417B2

Reaction notes

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