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

HRID 645315노트

반응식

HRID 645315 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a7d5cbae512148789854524e8b8422ca
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704409B2

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