Allyl bromide → 1-[2-(Allyloxy)-4-methylphenyl]ethanone

HRID 63957

반응식

HRID 63957 반응식
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C)C=O>[CH2:20]([O:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10])[CH:19]=[CH2:18]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 813382'-Hydroxy-4'-methylacetophenone

생성물 1

HCID 607470631-[2-(Allyloxy)-4-methylphenyl]ethanone수율 98%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1-(2-hydroxy-4-methyl-phenyl)-ethanone (10 g, 67 mmol) in dimethylformamide (100 mL) was added potassium carbonate (18.4 g, 133 mmol), followed by allyl bromide (5.75 mL, 67 mmol). The reaction was stirred at room temperature for 16 hours. The residue was partitioned between ethyl acetate (200 mL) and water (800 mL), the organics were separated, and washed with brine (50 mL), dried over MgSO4 and concentrated in vacuo. After cooling the concentrate to room temperature the title compound crystallised as colourless platelets, 12.40 g, in a 98% yield. LCMS (2 min acidic) 1.20 min 72-100% pure by UV, ES+/AP+ 191. 1HNMR (400 MHz, CDCl3) δ ppm 2.37 (s, 3H), 2.63 (s, 3H), 4.61-4.66 (m, 2H), 5.33 (dq, 1H), 5.44 (dq, 1H), 6.10 (m, 1H), 6.76 (s, 1H), 6.80-6.83 (m, 1H), 7.68 (d, 1H).

후처리

  1. customThe residue was partitioned between ethyl acetate (200 mL) and water (800 mL)
  2. customthe organics were separated
  3. washwashed with brine (50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. temperatureAfter cooling the
  7. concentrationconcentrate to room temperature the title compound
  8. customcrystallised as colourless platelets, 12.40 g, in a 98% yield
  9. customLCMS (2 min acidic) 1.20 min 72-100%

출처 및 근거

ORD 기록
ord-75359a5b606c485db38b74db2ae643ea
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447116B2

연결된 노트

불러오는 중…