Allyl bromide → Methyl 3-allyloxy-4-nitro-benzoate

HRID 354051

반응식

HRID 354051 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([OH:13])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CC(C)=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([O:13][CH2:23][CH:22]=[CH2:21])[CH:5]=1

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

생성물 1

HCID 59768302Methyl 3-allyloxy-4-nitro-benzoate수율 98.8%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 3-hydroxy-4-nitro-benzoic acid methyl ester (50.0 g, 253.6 mmol) in acetone (1 L) was added potassium carbonate (105.0 gram, 759.7 mmol) and allyl bromide (44.0 mL, 508.4 mmol). The reaction mixture was heated to reflux overnight and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give 3-allyloxy-4-nitro-benzoic acid methyl ester as solid (59.4 g, 98.8%). 1H NMR (CDCl3) δ3.96 (s, 3H), 4.75 (dt, 2H, J=5.0 Hz, 1.6 Hz), 5.36 (ddt, 1H, J=10.6 Hz, 1.4 Hz, 1.4 Hz), 5.50 (ddt, 1H, J=17.2 Hz, 1.6 Hz, 1.6 Hz), 6.05 (ddt, 1H, J=17.3 Hz, 10.6 Hz, 5.0 Hz), 7.69 (dd, 1H, J=8.33 Hz, 1.58 Hz), 7.75 (d, 1H, J=1.55 Hz), 7.83 (d, 1H, J=8.34 Hz).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customthe insoluble material was removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-66688ce691c142f68780be75658d2fed
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756395B2

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