N-bromobutanimide → Methyl 2-(bromomethyl)-3-nitrobenzoate

HRID 429224

反応式

HRID 429224 の反応式
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 601165Methyl 2-methyl-3-nitrobenzoate

生成物 1

HCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoate収率 93%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A stirred mixture of methyl 2-methyl-3-nitrobenzoate(17.6 g, 87.1 mmol) and N-bromosuccinimide (18.9 g, 105 mmol) in carbon tetrachloride (243 mL) was heated under gentle reflux with a 100 W light bulb situated 2 cm away shining on the reaction mixture overnight. After 18 hours, the reaction mixture was cooled to room temperature and filtered. The filtrate was washed with water (2×120 mL), brine(120 mL), and dried (MgSO4). The solvent was removed in vacuo to give a yellow solid. The product was purified by flash chromatography (hexane:ethyl acetate 8:2) to give 22 g (93%) of methyl 2-bromomethyl-3-nitrobenzoate as a yellow solid: mp 69-72° C.; 1H NMR (CDCl3) δ 8.13-8.09 (dd, J=1.36 and 7.86 Hz, 1H), 7.98-7.93 (dd, J=1.32 and 8.13 Hz, 1H), 7.57-7.51 (t, J=7.97Hz, 1H), 5.16 (s, 2H), 4.0 (s, 3H); 13C NMR (CDCl3) δ 65.84, 150.56, 134.68, 132.64, 132.36, 129.09, 53.05, 22.70; HPLC: Waters Nova-Pak C18 column, 4 micron, 1 mL/min, 240 nm, 40/60 CH3CN/0.1%H3PO4(aq), 8.2 min 99%. Anal. Calcd for C9H8NO4Br: C, 39.44; H, 2.94; N, 5.11, Br, 29.15. Found: C, 39.51; H, 2.79; N, 5.02; Br, 29.32.

後処理

  1. temperaturewas heated
  2. temperatureunder gentle reflux with a 100 W light bulb
  3. customaway shining on the reaction mixture overnight
  4. filtrationfiltered
  5. washThe filtrate was washed with water (2×120 mL), brine(120 mL)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customto give a yellow solid
  9. customThe product was purified by flash chromatography (hexane:ethyl acetate 8:2)

出典と根拠

ORDレコード
ord-ce7d540cd0f44707a337b0483b49db6a
出典データセット
uspto-grants-2001_11
特許番号
US06316471B1

関連ノート

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