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

HRID 10059노트

반응식

HRID 10059 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b650c99db20d4ba6b8fdcb17dc1d1211
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091353B2

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