Dichloromethane → HCID 86677538, compound

HRID 335055Notes

Reaction equation

HRID 335055 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:3]=1.[C:18](=O)([O-])[O-:19].[K+].[K+].C([B-](F)(F)F)=C.[K+].ClCCl>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.C1COCC1>[CH:18]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:3]=1)=[O:19]

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 12084039Methyl 1-methoxy-4-bromo-2-naphthoateHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 86677538HCID 86677538, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl 4-bromo-1-methoxy-2-naphthoate (see Example 2, 5.00 g, 16.9 mmol) in a 105 mL of a 20:1 mixture of THF:water under an atmosphere of nitrogen was added potassium carbonate (2.58 g, 18.6 mmol), potassium vinyltrifluoroborate (3.40 g, 25.4 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II), 1:1 complex with dichloromethane (1.24 g, 1.69 mmol). The reaction was heated at 65° C. for 65 hours, cooled to room temperature, diluted with ethyl acetate, and filtered through celite. The filtrate was concentrated in vacuo to provide methyl 4-formyl-1-methoxy-2-naphthoate that gave a mass ion (ES+) of 242.3 for [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-260e455568064d53b2807da0478d132f
Source dataset
uspto-grants-2014_11
Patent number
US08883850B2

Reaction notes

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