Benzoyl Peroxide → 7-(Bromomethyl)-5-nitrobenzofuran

HRID 1162044ノート

反応式

HRID 1162044 の反応式
[CH3:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:39])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:39][CH2:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

参加物

5

反応物 3

HCID 7187Benzoyl Peroxide2 回HCID 67184N-bromobutanimide2 回HCID 534029767-Methyl-5-nitro-1-benzofuran2 回

生成物 1

HCID 534029717-(Bromomethyl)-5-nitrobenzofuran

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
80 °C

実験手順

7-Methyl-5-nitro-1-benzofuran (2.1 g, 12 mmol; Intermediate 63) was dissolved in CCl4 and heated to 80° C. Benzoyl peroxide (0.43 g, 1.6 mmol) was added followed by NBS (2.1 g, 12 mmol) that was added in small portions. The reaction mixture was heated at reflux overnight with stirring. Additional benzoyl peroxide (0.08 mmol) and NBS (0.2 mmol) were added and the reaction mixture was stirred for one additional night. After this time, the mixture was filtered and concentrated. The crude was redissolved in DCM and washed with water. The organic solvent was dried (MgSO4) and evaporated. The residue was purified using preparative HPLC with a gradient of 45-70% MeCN. This afforded 0.7 g (22%) of 7-(bromomethyl)-5-nitro-benzofuran as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 4.78 (s, 2H) 6.96 (d, J=2.3 Hz, 1H) 7.84 (d, J=2.3 Hz, 1H) 8.28 (d, J=2.3 Hz, 1H) 8.49 (d, J=2.3 Hz, 1H). HPLC Rt=1.9 min (System A; 30-80% MeCN over 3 min ACE column).

後処理

  1. additionwas added in small portions
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux overnight
  4. stirringthe reaction mixture was stirred for one additional night
  5. filtrationAfter this time, the mixture was filtered
  6. concentrationconcentrated
  7. dissolutionThe crude was redissolved in DCM
  8. washwashed with water
  9. dry with materialThe organic solvent was dried (MgSO4)
  10. customevaporated
  11. customThe residue was purified

出典と根拠

ORDレコード
ord-89a5021b26ea461a9ee5ea6a95c4169d
出典データセット
uspto-grants-2010_10
特許番号
US07820675B2

反応ノート

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