Benzyl Bromide → 2-(Benzyloxy)-6-nitrobenzonitrile

HRID 471586노트

반응식

HRID 471586 반응식
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[N+:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([O:1][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:3]=1[C:4]#[N:5])([O-:12])=[O:11]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 125032052-Hydroxy-6-nitrobenzonitrile

생성물 1

HCID 203490242-(Benzyloxy)-6-nitrobenzonitrile수율 32.3%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 2-hydroxy-6-nitrobenzonitrile (Example 115) (1.0 g, 6.09 mmol) and Cs2CO3 (2.16 g, 6.64 mmol) in acetone (14 mL) was added benzyl bromide (1.16 g, 6.76 mmol). The reaction was refluxed under N2 for 1.5 hours, then filtered and the filtrate concentrated. The residue was purified by flash chromatography 3:2 Hexane:EtOAc to provide 2-nitro-6-(benzyloxy)benzonitrile (500 mg, 32%). 1H NMR (400 MHz, MeOD) δ 5.40 (s, 2H), 7.34-7.45 (m, 3H), 7.53 (m, 2H), 7.69 (dd, J=8.6, 0.8 Hz, 1H), 7.82 (t, J=8.4 Hz, 1H), 7.91 (t, J=8.2, 0.8 Hz, 1H).

후처리

  1. temperatureThe reaction was refluxed under N2 for 1.5 hours
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated
  4. customThe residue was purified by flash chromatography 3:2 Hexane

출처 및 근거

ORD 기록
ord-baa2cabc85c9464b99363ef6dda6e976
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633186B2

반응 노트

불러오는 중…