7-Bromo-3-methylnaphthalen-1-ol → 1-Naphthol, 3-methyl-

HRID 926203

반응식

HRID 926203 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:13])[CH:8]=[C:9]2[OH:12])=[CH:4][CH:3]=1>[Pd].CCO>[CH3:13][C:7]1[CH:8]=[C:9]([OH:12])[C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[CH:2][CH:11]=2

참가 물질

4

반응물 1

HCID 671262827-Bromo-3-methylnaphthalen-1-ol

생성물 1

HCID 261351-Naphthol, 3-methyl-

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

반응 조건

온도
23 °C

실험 절차

A slurry of 7-bromo-3-methylnaphthalen-1-ol (100 mg, 0.421 mmol), 10% w/w Pd/C (45 mg, 42.1 μmol Pd), and absolute EtOH (2.0 mL) was purged under vacuum and backfilled with H2 from a balloon several times. The suspension was stirred under a balloon of H2 at 23° C. overnight. The reaction was filtered over Celite, the cake was washed with EtOAc. The filtrate was concentrated and dissolved in DCM. The solution was loaded onto a 12 g “gold” ISCO silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product. 1H NMR (400 MHz, CDCl3) δ 8.10 (d, J=7.8 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.47-7.39 (m, 2H), 7.22 (s, 1H), 6.67 (s, 1H), 2.45 (s, 3H).

후처리

  1. filtrationThe reaction was filtered over Celite
  2. washthe cake was washed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutiondissolved in DCM
  5. custompurified by flash chromatography (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-3ce10ff026c24790bc283c48f3f74460
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284323B2

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