Ammonium Chloride → 2-Methoxy-1-phenylnaphthalene

HRID 387490

반응식

HRID 387490 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C.C(COC)OC.O>[CH3:13][O:12][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

10

반응물 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 728601-Bromo-2-methoxynaphthalene

생성물 1

HCID 113222662-Methoxy-1-phenylnaphthalene수율 66%

시약·촉매·용매 5

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a flask charged with 1-bromo-2-methoxynaphthalene (20.0 g, 84.4 mmol), phenylboronic acid (11.3 g, 92.8 mmol), palladium acetate (0.10 g, 0.46 mmol), triphenylphosphine (0.85 g, 2.78 mmol) and potassium phosphate (40.9 g, 177.9 mmol), added was mixture of water (60 mL) and dimethoxyethane (120 mL), and the resultant mixture was heated under reflux for 6 hours. After cooling the mixture to ambient temperature, aqueous ammonium chloride solution (150 mL) and diethyl ether (200 mL) were injected thereto. The organic layer was isolated, and the residue was extracted with diethyl ether. The combined organic layer was dried over magnesium sulfate and evaporated to remove the volatile substances. Purification via silica gel column chromatography (n-hexane) gave 2-methoxy-1-phenylnaphthalene (13.0 g, yield: 66%) as colorless liquid.

후처리

  1. additionadded
  2. temperatureunder reflux for 6 hours
  3. customThe organic layer was isolated
  4. extractionthe residue was extracted with diethyl ether
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. customevaporated
  7. customto remove the volatile substances
  8. customPurification via silica gel column chromatography (n-hexane)

출처 및 근거

ORD 기록
ord-36571d0ab94e4cce8539905db4773d03
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372996B2

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