N-bromobutanimide → Methyl 3-bromo-2-(bromomethyl)benzoate

HRID 10059ノート

反応式

HRID 10059 の反応式
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Br:13]N1C(=O)CCC1=O>C(#N)C>[Br:1][C:2]1[C:3]([CH2:12][Br:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 12929135Methyl 3-Bromo-2-methylbenzoate

生成物 1

HCID 21907554Methyl 3-bromo-2-(bromomethyl)benzoate収率 107.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of methyl 3-bromo-2-methylbenzoate (17.0 g, 74.22 mmol) and N-bromosuccinimide (15.85 g, 89.06 mmol) in acetonitrile (200 mL) was heated under gently refluxing for 17 hours while a 200 W bulb situated 2 cm away was shining on the reaction flask. The mixture was cooled to room temperature and solvent was removed. The residue was dissolved in ethyl acetate (200 mL) and washed with water (3×80 mL), brine (80 mL) and dried (MgSO4). Solvent was removed to give methyl 3-bromo-2-bromomethylbenzoate (24.5 g, 97% by HPLC): 1H NMR (CDCl3) δ 7.90–7.86 (dd, J=1.0 and 7.9 Hz, 1H), 7.78–7.74 (dd, J=1.2 and 8.2 Hz, 1H), 7.22 (t, J=7.9 Hz, 1H), 5.12 (s, 2H), 3.95 (s, 3H).

後処理

  1. temperaturewas heated
  2. temperatureunder gently refluxing for 17 hours while a 200 W bulb
  3. customsolvent was removed
  4. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  5. washwashed with water (3×80 mL), brine (80 mL)
  6. dry with materialdried (MgSO4)
  7. customSolvent was removed

出典と根拠

ORDレコード
ord-b650c99db20d4ba6b8fdcb17dc1d1211
出典データセット
uspto-grants-2006_08
特許番号
US07091353B2

反応ノート

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