Ammonium Chloride → 2-Methoxy-1-phenylnaphthalene

HRID 563454

반응식

HRID 563454 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

In 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), mixture of water (60 mL) and dimethoxyethane (120 mL) was added, and the resultant mixture was heated under reflux for 6 hours. After cooling to ambient temperature, aqueous ammonium chloride (150 mL) and diethyl ether (200 mL) were charged thereto. The organic layer was isolated, and the residue was extracted with diethyl ether. Combined organic layer was dried over magnesium sulfate, and evaporated to remove the volatiles. Purification via silica gel column chromatography (eluent: hexane) gave 2-methoxy-1-phenylnaphthalene (13.0 g, yield: 66%) as colorless liquid.

후처리

  1. additionwas added
  2. temperatureunder reflux for 6 hours
  3. customThe organic layer was isolated
  4. extractionthe residue was extracted with diethyl ether
  5. dry with materialCombined organic layer was dried over magnesium sulfate
  6. customevaporated
  7. customto remove the volatiles
  8. customPurification via silica gel column chromatography (eluent: hexane)

출처 및 근거

ORD 기록
ord-478e6e1c71fe4c42a26002ea40ca122f
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067511B2

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