Water → 2-Bromo-6-ethoxynaphthalene

HRID 270139

反応式

HRID 270139 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([OH:14])[CH:8]=[CH:7]2.[CH2:15](I)[CH3:16].O>CN(C=O)C>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH2:15][CH3:16])[CH:10]=2)[CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 271446-Bromo-2-naphthalenol

生成物 1

HCID 2368582-Bromo-6-ethoxynaphthalene収率 60%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of sodium hydride (800 mg, 60% oil dispersion) in DMF (20 ml) was added a solution of 6-Bromo-2-naphthol dropwise with stirring at 0°. After gas evolution had ceased, neat ethyl iodide (1.6 ml) was added dropwise to the stirred solution. The reaction was stirred overnight at rt. The reaction mixture was poured into water and extracted several times with tert-butyl methyl ether. The combined organic extracts were washed with water and brine, then dried over MgSO4, filtered and evaporated under reduced pressure to give tan solid. This was recrystallized from MeOH and dried under high vacuum to a constant wt. giving a white solid (3.11 g, 60%). 1H NMR(400 MHz, CDCl3) δ 7.92 (d, J=1.7 Hz, 1H), 7.65(d, J=8.9 Hz, 1H), 7.59 (d, J=8.7 Hz, 2H), 7.16 (dd, J=8.9 Hz, 2.48, 1H), 7.09 (d, J=2.4 Hz, 1H), 4.15 (q, 2H), 1.49 (t, 3H).

後処理

  1. stirringThe reaction was stirred overnight at rt
  2. extractionextracted several times with tert-butyl methyl ether
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give tan solid
  8. customThis was recrystallized from MeOH
  9. customdried under high vacuum to a constant wt.

出典と根拠

ORDレコード
ord-df828a1b05814f0a87eca2d241c0fd3d
出典データセット
uspto-grants-2008_11
特許番号
US07449484B2

関連ノート

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