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

HRID 471586ノート

反応式

HRID 471586 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 203490242-(Benzyloxy)-6-nitrobenzonitrile収率 32.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-baa2cabc85c9464b99363ef6dda6e976
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

反応ノート

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