Potassium Acetate → HCID 22728212, compound

HRID 2086129Notes

Reaction equation

HRID 2086129 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[C:15]2[C:10](=[C:11]([O:16][CH3:17])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.C([O-])(=O)C.[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C(=O)C>[CH3:17][O:16][C:11]1[C:10]2=[CH:9][CH:8]=[C:7]3[C:6]([O:5][CH2:4][C:3]4[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:2]3=4)=[C:15]2[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 22728210HCID 22728210, compound

Product 1

HCID 22728212HCID 22728212, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

To a 2000 ml recovery flask was added 1-[(2-bromo-5-methoxybenzyl)oxy]-5-methoxynaphthalene (3.0 g, 8.03 mmol), potassium acetate (2.4 g anh., 24.10 mmol), PdCl2(PPh3)2 (1.12 g, 1.60 mmol), and N,N-dimethylacetamide (500 ml 99%). The flask was purged with nitrogen, heated to 130° C. for 12 h, and concentrated under high vacuum. The dark solids were then dissolved in ether/CH2Cl2 (1/1 300 ml) and passed through a silica gel/celite plug. Evaporation under reduced pressure afforded 2.32 g (99%) product as a tan colored solid. mp 166-167° C.; 1H NMR (300 MHz, DMSO-d6) δ 3.82 (3H, s), 3.97 (3H, s), 5.30 (2H, s), 6.98 (3H, m), 7.42 (1H, t, J=8.1 Hz), 7.69 (1H, d, J=8.5 Hz), 7.81 (2H, appd, J=8.6 Hz), 7.91 (1H, d, J=8.9 Hz); MS m/z 293 (M+H+).

Workup

  1. customThe flask was purged with nitrogen
  2. concentrationconcentrated under high vacuum
  3. dissolutionThe dark solids were then dissolved in ether/CH2Cl2 (1/1 300 ml)
  4. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-1fc2eb180e454966ac49c54864540b3c
Source dataset
uspto-grants-2004_04
Patent number
US06723747B2

Reaction notes

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