Water → 2-Bromo-6-ethoxynaphthalene

HRID 270139

반응식

HRID 270139 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 2368582-Bromo-6-ethoxynaphthalene수율 60%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-df828a1b05814f0a87eca2d241c0fd3d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449484B2

연결된 노트

불러오는 중…