Allyl bromide → 2-(Allyloxy)-1-bromo-5-methyl-3-nitrobenzene

HRID 1373766

반응식

HRID 1373766 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CC(C)=O>[CH2:21]([O:12][C:3]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[Br:1])[CH:20]=[CH2:19]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 299182-Bromo-4-methyl-6-nitrophenol

생성물 1

HCID 149774442-(Allyloxy)-1-bromo-5-methyl-3-nitrobenzene수율 94.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a mixture of 2-bromo-4-methyl-6-nitrophenol (7.00 g, 30.2 mmol), K2CO3 (6.26 g, 45.3 mmol) in acetone (105 mL) was added allyl bromide (3.80 ml, 45.3 mmol). The reaction mixture was stirred at room temperature overnight. It was then heated at 40° C. for 5 hrs. Inorganic salts were filtered and washed with acetone. The filtrate was concentrated to give 7.74 g (94%) of the desired product. MS (DCI/NH3) m/z: 289.0 (M+NH4)+; 1H NMR (300 MHz, CD3OD) δ ppm 2.37 (s, 3 H) 4.61 (d, J=6.10 Hz, 2 H) 5.26 (dd, J=10.51, 1.80 Hz, 1 H) 5.39 (dd, J=17.29, 1.80 Hz, 1 H) 6.09 (m, 1 H) 7.63 (s, 1 H) 7.74 (s, 1 H).

후처리

  1. temperatureIt was then heated at 40° C. for 5 hrs
  2. filtrationInorganic salts were filtered
  3. washwashed with acetone
  4. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-45249ef8d80d45258c2767c58c8dce87
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07163939B2

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