Sodium Acetate → HCID 21071808, compound

HRID 1372177Notes

Reaction equation

HRID 1372177 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 (2 H, 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-2491fa82e7c64307b697fc678f5684cc
Source dataset
uspto-grants-2007_01
Patent number
US07157492B2

Reaction notes

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