Hydrogen Bromide → 1-Bromo 4-fluoronaphthalene

HRID 322047

반응식

HRID 322047 반응식
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Br:12]Br.Br>C(Cl)(Cl)(Cl)Cl>[Br:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([F:1])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 260Hydrogen BromideHCID 94501-FluoronaphthaleneHCID 24408Bromine

생성물 1

HCID 676471-Bromo 4-fluoronaphthalene

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a 50 mL round-bottomed flask equipped with condenser and N2 inlet were added 3.75 mL (5.0 g, 34.25 mmol) 1-fluoronaphthalene and 10 mL carbon tetrachloride, followed by dropwise addition of 1.7 mL (5.5 g., 34.375 mmol) bromine over 3 min. The reaction was heated to 50-60° C. as HBr was evolved for 2 hour, then cooled and concentrated. The residue was dissolved in methanol and kept overnight at 0° C. After filtration with cold methanol, the product, with melting point close to room temperature, was 4.62 g (60%) of a yellow oil. 1H-NMR (δ, CDCl3): 7.02 (t, J=8, 1H), 7.6-7.7 (m, 3H), 8.10 (d, J=8.5, 1H), 8.20 (d, J=8.5, 1H); GCMS (%): 224/226 (parent, Br79/Br81 100).

후처리

  1. customTo a 50 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperaturecooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in methanol
  5. waitkept overnight at 0° C
  6. filtrationAfter filtration with cold methanol
  7. customclose to room temperature

출처 및 근거

ORD 기록
ord-906272ed9be645bdbd2424f78382d66a
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211208B1

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