1-Bromo-2-naphthol → HCID 50992704, compound

HRID 1912162Notes

Reaction equation

HRID 1912162 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[OH:22].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[OH:22]

Participants

8

Reactant 4

HCID 113161-Bromo-2-naphtholHCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 50992704HCID 50992704, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Into a 200 mL three-neck flask were placed 1.4 g (10 mmol) of 2-fluorophenylboronic acid, 2.2 g (10 mmol) of 1-bromo-2-naphthol, 153 mg (0.50 mmol) of tri(ortho-tolyl)phosphine, 25 mL of toluene, 25 mL of ethanol, and 5.0 mL of a 2M aqueous solution of potassium carbonate. This mixture was degassed under reduced pressure, and the air in the system was replaced with nitrogen. This mixture was stirred at 80° C., 23 mg (0.10 mmol) of palladium(II) acetate was added thereto, and the mixture was refluxed at about 100° C. for 6.5 hours. After the reflux, this mixture was washed with water, and the aqueous layer was subjected to extraction with ethyl acetate. The obtained solution of the extract and the organic layer were combined and washed with saturated brine. The obtained organic layer was dried over magnesium sulfate. This mixture was gravity-filtered, and the obtained filtrate was concentrated to give a brown oily substance. This oily substance was purified by silica gel column chromatography (developing solvent: toluene), so that 1.6 g of a brown oily substance of the object of the synthesis was obtained in 69% yield. The above-described synthesis, scheme is illustrated in the following scheme (B-1).

Workup

  1. customInto a 200 mL three-neck flask were placed
  2. customThis mixture was degassed under reduced pressure
  3. temperaturethe mixture was refluxed at about 100° C. for 6.5 hours
  4. washAfter the reflux, this mixture was washed with water
  5. extractionthe aqueous layer was subjected to extraction with ethyl acetate
  6. extractionThe obtained solution of the extract
  7. washwashed with saturated brine
  8. dry with materialThe obtained organic layer was dried over magnesium sulfate
  9. filtrationThis mixture was gravity-filtered
  10. concentrationthe obtained filtrate was concentrated
  11. customto give a brown oily substance
  12. customThis oily substance was purified by silica gel column chromatography (developing solvent: toluene), so that 1.6 g of a brown oily substance of the object of the synthesis
  13. customwas obtained in 69% yield
  14. customThe above-described synthesis, scheme

Sources & evidence

ORD record
ord-2f9534a6f4a74151b3f922c791a539b2
Source dataset
uspto-grants-2013_12
Patent number
US08604224B2

Reaction notes

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