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

HRID 2221442

반응식

HRID 2221442 반응식
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:15][CH2:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 74953Methyl 3-methyl-2-benzofurancarboxylate

생성물 1

HCID 100838Methyl 3-(bromomethyl)-2-benzofurancarboxylate수율 108.7%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A solution of methyl 3-methylbenzofuran-2-carboxylate (1.0 g, 5.3 mmol), N-bromosuccinimide (0.95 g, 5.3 mmol) and 2,2′-azobisisobutyronitrile (87 mg, 0.53 mmol) was heated to reflux in CCl4 (40 ml) for 3 h, then cooled to room temperature and concentrated. The residue was dissolved in ethyl acetate (100 ml) and washed with water (100 ml). The organic layer was dried over magnesium sulfate and concentrated to provide crude methyl 3-bromomethylbenzofuran-2-carboxylate (1.55 g) as a yellowish solid, which was used in the next step without further purification.

후처리

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  3. washwashed with water (100 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8cf3f5e8500348a69a4705b088f22356
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368572B2

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