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

HRID 1060230

反応式

HRID 1060230 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 135756662-(Allyloxy)-4-methyl-1-nitrobenzene収率 95%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e937650471254c9ca85f73f03af6a602
出典データセット
uspto-grants-2003_02
特許番号
US06521663B2

関連ノート

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