Allyl bromide → 2-(Allyloxy)-4-methyl-1-nitrobenzene

HRID 1060230

반응식

HRID 1060230 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH2:14][CH:13]=[CH2:12])[CH:7]=1

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 127886-Nitro-m-cresol

생성물 1

HCID 135756662-(Allyloxy)-4-methyl-1-nitrobenzene수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-methyl-2-nitrophenol (2.00 g, 13.1 mmol), allyl bromide (1.30 mL, 15.0 mmol), and cesium carbonate (5.5 g, 17 mmol) in DMF (100 mL) was stirred at ambient temperature. After 20 hrs the reaction was filtered, frit washed with methanol, and the filtrate evaporated in vacuo at 50° C. The residue was purified by flash column chromatography (4:1 then 2:1 hexane:ethyl acetate eluant) giving the title compound as a yellow oil (2.39 g, 95%) that crystallized after sitting 3 days at ambient temperature. 1H NMR (300 Mz, DCl3) δ 7.79 (d, 1H, J=8.2 Hz), 6.86 (s, 1H), 6.82 (m, 1H), 6.05 (ddt, 1H, J=17.3 Hz, 10.6 Hz, 5.0 Hz), 5.50 (ddd, 1H, J=17.3 Hz, 3.3 Hz, 1.7 Hz), 5.33 (ddd, 1H, J=10.6 Hz, 2.9 Hz, 1.5 Hz), 4.67 (dt, 2H, J=4,9 Hz, 1.6 Hz), 2.40 (s, 3H).

후처리

  1. filtrationAfter 20 hrs the reaction was filtered
  2. washfrit washed with methanol
  3. customthe filtrate evaporated in vacuo at 50° C
  4. customThe residue was purified by flash column chromatography (4:1

출처 및 근거

ORD 기록
ord-e937650471254c9ca85f73f03af6a602
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521663B2

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