Hydrochloric Acid → HCID 67607343, compound

HRID 2274136Notes

Reaction equation

HRID 2274136 reaction equation
[CH:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[C:3](B(O)O)[CH:2]=1.Br[C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([OH:31])[CH:25]=[CH:24]2.C(=O)([O-])[O-].[Na+].[Na+].Cl>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=[C:3]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[C:26]([OH:31])[CH:25]=[CH:24]3)[CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 271446-Bromo-2-naphthalenolHCID 23088535Fluoranthen-3-ylboronic acid

Product 1

HCID 67607343HCID 67607343, compoundYield 89.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under the atmosphere of argon, 2.7 g of fluoranthene-3-boronic acid, 2.0 g of 6-bromo-2-naphthol, 0.31 g of tetrakis(triphenylphosphine)palladium (0), 27 mL of 1,2-dimethoxyethane and 13.5 mL of an aqueous 2M sodium carbonate solution were placed in a flask, and the resulting mixture was stirred under reflux while heating for 4 hours. After cooling to room temperature, 2M hydrochloric acid was added to the reaction solution to allow it to be acidic, and the reaction solution was extracted with dichloromethane. An aqueous phase was removed and an organic phase was washed with saturated saline, and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, residues were dispersed and washed with dichloromethane, whereby 2.75 g (yield 89%) of 6-(fluoranthen-3-yl)-2-naphthol as an intended product was obtained.

Workup

  1. temperatureunder reflux
  2. temperaturewhile heating for 4 hours
  3. extractionthe reaction solution was extracted with dichloromethane
  4. customAn aqueous phase was removed
  5. washan organic phase was washed with saturated saline
  6. dry with materialdried with anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off under reduced pressure, residues
  9. additionwere dispersed

Sources & evidence

ORD record
ord-15ca47a75e064c1b9549e6405a7603d5
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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