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Sodium Carbonate → 6-(3-Phenyl-4-methoxyphenyl)-2-naphthaldehyde

HRID 860551
Notes
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Reaction equation

HRID 860551 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([CH:29]=[O:30])[CH:23]=[CH:22]2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.[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>[C:1]1([C:7]2[CH:8]=[C:9]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[CH:25]=[C:24]([CH:29]=[O:30])[CH:23]=[CH:22]4)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 134770296-Bromonaphthalene-2-carbaldehydeHCID 21037383(4-Methoxy-3-phenylphenyl)boronic acid

Product 1

HCID 865860406-(3-Phenyl-4-methoxyphenyl)-2-naphthaldehydeYield 86.9%

Reagents, catalysts & solvents 4

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent
HCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 3-phenyl-4-methoxyphenyl boronic acid (0.465 g, 2.04 mmol), 6-bromo-2-naphthaldehyde (0.400 g, 1.70 mmol) and sodium carbonate (0.541 g, 5.10 mmol) in 10 mL of toluene:ethanol (4:1) and water (1 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine) palladium(0) (0.059 g, 0.05 mmol) was added and the mixture heated at reflux for 17 hours. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: hexane:EtOAc, 9:1) to give 0.50 g of 6-(3-phenyl-4-methoxyphenyl)-2-naphthaldehyde (86%) as a solid. 1H NMR (300 MHz; DMSO-d6, 300 MHz): δ 3.90 (s, 3H), 7.12 (d, J=9.0 Hz, 1H), 7.33–7.50 (m, 3H), 7.55-7.65 (m, 2H), 7.68–7.75 (m, 2H), 7.87 (dd, J1=8.4 Hz, J2=1.8 Hz, 1H), 7.97 (brs, 2H), 8.06 (d, J=9.0 Hz, 1H), 8.09 (d, J=1.0 Hz, 1H), 8.35 (s, 1H), 10.16 (s, 1H).

Workup

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux for 17 hours
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (eluent: hexane:EtOAc, 9:1)

Sources & evidence

ORD record
ord-dc4bf5aa10404bcba510fa2354abd673
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07153875B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes