Potassium Phosphate, Tribasic → 1-Methoxy-5-methylnaphthalene

HRID 1470487Notes

Reaction equation

HRID 1470487 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[C:12]([O:17][CH3:18])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)(=O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:29]B(O)O.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[NH4+].[Cl-].CC([O-])=O.CC([O-])=O.[Pd+2].O.C1(C)C=CC=CC=1>[CH3:18][O:17][C:12]1[C:11]2[C:16](=[C:7]([CH3:29])[CH:8]=[CH:9][CH:10]=2)[CH:15]=[CH:14][CH:13]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 634876Binap, (A+-)-HCID 110667265-Methoxynaphthalen-1-yl trifluoromethanesulfonate

Product 1

HCID 109759531-Methoxy-5-methylnaphthaleneYield 88.8%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

In a 500 mL 2-neck round bottom flask, toluene (300 mL) and deionized water (14 mL) were added and degassed under nitrogen for 20 minutes. Then, 5-methoxynaphthalen-1-yl trifluoromethanesulfonate (above Step-2 intermediate) (14 g, 45.75 mmol) was added to the above mixture. After stirring for 10 min at RT, K3PO4 (34 g, 160 mmol) and methylboronic acid (4.1 g, 68.6 mmol) were added followed by Pd(OAc)2 (1.03 g, 4.6 mmol) and BINAP (5.7 g, 9.15 mmol) and the reaction mixture was stirred at RT for 15 min under nitrogen and then heated to 100° C. overnight. It was cooled and diluted with saturated NH4Cl solution (150 mL). The aqueous layer was extracted with EtOAc (4×100 mL) and the combined organic layer was washed with water (100 mL), brine (100 mL), dried and filtered. After solvent removal, the crude product obtained was purified by column chromatography (5% EtOAc:Hexanes) to yield the desired compound (7 g, 87%) as a white solid.

Workup

  1. customdegassed under nitrogen for 20 minutes
  2. stirringthe reaction mixture was stirred at RT for 15 min under nitrogen
  3. temperatureheated to 100° C. overnight
  4. temperatureIt was cooled
  5. extractionThe aqueous layer was extracted with EtOAc (4×100 mL)
  6. washthe combined organic layer was washed with water (100 mL), brine (100 mL)
  7. customdried
  8. filtrationfiltered
  9. customAfter solvent removal
  10. customthe crude product obtained
  11. customwas purified by column chromatography (5% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-3c01cd9ab524490eb81a81603ffbe48d
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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