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Ammonium Chloride → 2-Methoxy-1-phenylnaphthalene

HRID 387490
Notes
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Reaction equation

HRID 387490 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

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

Product 1

HCID 113222662-Methoxy-1-phenylnaphthaleneYield 66%

Reagents, catalysts & solvents 5

HCID 11776
Triphenylphosphine
Catalyst
HCID 167845palladium(II) acetateCatalyst
HCID 962WaterSolvent
HCID 3283Diethyl EtherSolvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-36571d0ab94e4cce8539905db4773d03
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372996B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes