1-Naphthol → 4-Bromonaphthalen-1-ol

HRID 1644214노트

반응식

HRID 1644214 반응식
[CH:1]1[CH:2]=[CH:3][C:4]2[C:5](=[CH:7][CH:8]=[CH:9][C:10]=2[OH:11])[CH:6]=1.[Br:12]N1C(=O)CCC1=O>CC#N>[Br:12][C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:10]([OH:11])=[CH:9][CH:8]=1

참가 물질

4

반응물 2

HCID 70051-NaphtholHCID 67184N-bromobutanimide

생성물 1

HCID 5756094-Bromonaphthalen-1-ol수율 64%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of naphthol (12, 5.0 g, 35 mmol) in CH3CN (125 mL) at 0° C. was added N-bromosuccinimide (7.9 g, 45 mmole) in several portions. The reaction mixture was warmed to room temperature, stirred for 1 h, and concentrated. The residue was dissolved in EtOAc (500 mL) and the solution was washed with water (300 mL) and brine (300 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (silica gel, 4:1 hexanes/EtOAc) to afford 4-bromonaphthol (13, 5.0 g, 64%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.22-8.16 (m, 2H), 7.62-7.26 (m, 3H), 6.71 (d, J=8.0 Hz, 1H), 5.46 (s, 1H).

후처리

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in EtOAc (500 mL)
  3. washthe solution was washed with water (300 mL) and brine (300 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel, 4:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-3e50b182f21b4a688e5b4c737faa7dc3
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124607B2

반응 노트

불러오는 중…