Sodium Carbonate → HCID 58763497, compound

HRID 625613Notes

Reaction equation

HRID 625613 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18](=[O:20])[CH3:19])[CH:12]=[CH:11]2.[C:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])[CH3:22]>O.C1(C)C=CC=CC=1.C(O)C.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>[C:18]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:27]1[CH:28]=[CH:29][C:24]([C:21](=[O:23])[CH3:22])=[CH:25][CH:26]=1)[CH:17]=[CH:16]2)(=[O:20])[CH3:19]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 37021224-Acetylphenylboronic acidHCID 124330821-(6-Bromonaphthalen-2-yl)ethanone

Product 1

HCID 58763497HCID 58763497, compoundYield 62.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A solution of sodium carbonate (5.43 g, 51.3 mmol) in water (35 mL) was added to a stirred solution of 1-(6-bromonaphthalen-2-yl)ethanone (2.554 g, 10.25 mmol) and 4-acetylphenylboronic acid (2.017 g, 12.30 mmol) in toluene (35.0 mL) and ethanol (35.0 mL) and nitrogen was bubbled through the reaction mixture for 15 min. Then Pd(PPh3)4 (0.237 g, 0.205 mmol) was added, and the reaction was flushed with nitrogen and heated at 95° C. under nitrogen for 8 h and then stirred overnight at rt. The reaction was concentrated to dryness under high vacuum and then partitioned between DCM (˜200 mL) and water (˜150 mL). The organic layer was then washed with brine (˜100 mL), dried (MsSO4), filtered and concentrated. The residue was triturated with MeOH (˜120 mL) and the remaining solids were redissolved into DCM and concentrated to dryness (˜2.7 g of orange solid). This material was dissolved into hot EtOAc (80 mL) and allowed to cool. The resulting solids were collected by filtration and rinsed with Et2O to yield 1-(4-(6-acetylnaphthalen-2-yl)phenyl)ethanone (1.84 g). LC-MS retention time 2.443 min; m/z 288.98 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 10u C18 3.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where Solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and Solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a MICROMASS® Platform for LC in electrospray mode. 1H NMR (400 MHz, chloroform-d) δ ppm 8.51 (s, 1H), 8.05-8.16 (m, 5H), 7.98 (d, J=8.8 Hz, 1H), 7.81-7.88 (m, 3H), 2.76 (s, 3H), 2.68 (s, 3H).

Workup

  1. customwas bubbled through the reaction mixture for 15 min
  2. customthe reaction was flushed with nitrogen
  3. concentrationThe reaction was concentrated to dryness under high vacuum
  4. custompartitioned between DCM (˜200 mL) and water (˜150 mL)
  5. washThe organic layer was then washed with brine (˜100 mL)
  6. customdried (MsSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was triturated with MeOH (˜120 mL)
  10. dissolutionthe remaining solids were redissolved into DCM
  11. concentrationconcentrated to dryness (˜2.7 g of orange solid)
  12. dissolutionThis material was dissolved into hot EtOAc (80 mL)
  13. temperatureto cool
  14. filtrationThe resulting solids were collected by filtration
  15. washrinsed with Et2O

Sources & evidence

ORD record
ord-f0da24f90dbe400081ee7905279b6eb4
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

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