Toluene → (E)-methyl 4-styryl-1-naphthoate

HRID 1950712Notes

Reaction equation

HRID 1950712 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[C:23]1(/[CH:29]=[CH:30]/B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>C(O)C.CCOC(C)=O.O.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]>[CH:30](/[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1)=[CH:29]\[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 5702628Styrylboronic acidHCID 22711886Methyl 4-bromo-1-naphthoate

Product 1

HCID 66824254(E)-methyl 4-styryl-1-naphthoate

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-bromo-1-naphthoate, (Preparation 1, 5.4 g, 20.4 mmol) in ethanol (50 mL) and toluene (50 mL) was added Pd(dppf)2Cl2 (760 mg, 1.0 mmol), trans-2-phenylvinylboronic acid (3.3 g, 22.4 mmol) and sodium bicarbonate aqueous solution (40 mL of 2M solution). The mixture was heated to reflux for 3 hours. The mixture was cooled to room temperature and diluted with EtOAc (150 mL) and water (75 mL). The organic phase was separated, washed with brine (50 mL), dried over sodium sulfate, and concentrated. The residue was purified by chromatography on silica gel eluting from 10:90 EtOAc:heptane to 50:50 EtOAc:heptane to afford an oil which solidified upon standing (5.3 g, 90%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe organic phase was separated
  4. washwashed with brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel eluting from 10:90 EtOAc
  8. customheptane to 50:50 EtOAc:heptane to afford an oil which

Sources & evidence

ORD record
ord-00b36cf1d51f47d58fff69e9d7adcd6a
Source dataset
uspto-grants-2013_03
Patent number
US08404649B2

Reaction notes

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