2-Bromopropane → HCID 22145278, compound

HRID 1359471Notes

Reaction equation

HRID 1359471 reaction equation
O[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.C(=O)([O-])[O-:15].[Cs+].[Cs+].Br[CH:21]([CH3:23])[CH3:22]>CN(C)C=O>[CH:21]([O:15][C:7]1[C:8]2[C:3](=[CH:2][C:11]([O:12][CH3:13])=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 109975355-hydroxy-6-methoxynaphthalene

Product 1

HCID 22145278HCID 22145278, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 5-hydroxy-6-methoxynaphthalene (2.10 g, 12.1 mmole), cesium carbonate (19.7 g, 60.5 mmole), N,N-dimethylformamide (12 ml) and 2-bromopropane (3.50 ml, 36.9 mmole) was stirred in a 40° C. oil bath overnight. The reaction mixture was filtered and the solid residue was rinsed thoroughly with ethyl ether. The filtrate and the washings were combined and concentrated in vacuo to remove most of the solvents. The brown residue was partitioned between water and ether and the layers were separated. The ether layer was washed with water. The combined aqueous layers were back extracted with ether. The ether extracts were combined, washed with brine and dried over sodium sulfate. Filtration and concentration gave a crude which was purified by column chromatography (2.5→5% ethyl acetate/hexanes) to give 1-isopropoxy-6-methoxynaphthalene (2.23 g, 86% yield) as a light brown oil. 1H NMR (CDCl3) δ8.17 (1H, d, phenyl), 7.05-7.38 (4H, m, phenyl), 6.72 (1H, dd, phenyl), 4.73 (1H, m, CH of iPr), 3.92 (3H, s, OCH3), 1.42 (6H, d, 2 CH3 of iPr).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solid residue was rinsed thoroughly with ethyl ether
  3. concentrationconcentrated in vacuo
  4. customto remove most of the solvents
  5. customThe brown residue was partitioned between water and ether
  6. customthe layers were separated
  7. washThe ether layer was washed with water
  8. extractionThe combined aqueous layers were back extracted with ether
  9. washwashed with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationFiltration and concentration
  12. customgave a crude which
  13. customwas purified by column chromatography (2.5→5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-12198f7b07014582a4bf3182dfd34048
Source dataset
uspto-grants-2003_07
Patent number
US06600015B2

Reaction notes

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