Sodium Acetate → HCID 21071808, compound

HRID 2242395Notes

Reaction equation

HRID 2242395 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[CH:11][CH:12]=2)[CH:7]=1.C([O-])(=O)C.[Na+]>CC(N(C)C)=O>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:2]2[C:15]3[CH:14]=[C:13]4[CH:12]=[CH:11][C:10]([O:16][CH3:17])=[CH:9][C:8]4=[CH:7][C:6]=3[O:5][CH2:4][C:3]=2[CH:18]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 21071807HCID 21071807, compound

Product 1

HCID 21071808HCID 21071808, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-[(2-bromo-5-methoxybenzyl)oxy]-7-methoxynaphthalene (9.35 g, 25 mmol), dichlorobis(triphenylphosphine) palladium (1.75 g, 2.5 mmol), and sodium acetate (6.15 g, 75 mmol) in anhydrous dimethylacetamide (500 mL) was stirred at 130° C. under nitrogen for two days. After cooling, the catalyst was filtered off and the dimethylacetamide removed under vacuum. The residue was slurried in methanol (200 mL) and the desired product was isolated by filtration to afford 2.9 g (40%) of a tan solid: mp 190-191° C.; 1H NMR (DMSO-d6): δ 3.81 (3H, s), 3.85 (3H, s), 5.14 (2H, s), 6.92 (1H, d, J=2.6 Hz), 7.00-7.03 (2H, m), 7.18 (1H, d, J=2.4 Hz), 7.29 (1H, s), 7.79 (1H, d, J=9.0 Hz), 7.92 (1H, d, J=8.7 Hz), 8.26 (1H, s); MS m/z 293 ([M+H]+).

Workup

  1. temperatureAfter cooling
  2. filtrationthe catalyst was filtered off
  3. customthe dimethylacetamide removed under vacuum

Sources & evidence

ORD record
ord-a2721328d5cf4f8a856970e5cfbadaa9
Source dataset
uspto-grants-2010_03
Patent number
US07671084B2

Reaction notes

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