N-bromobutanimide → Methyl 2-(bromomethyl)-5-ethoxybenzoate

HRID 577594노트

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HRID 577594 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])[CH3:2].C1C(=O)N([Br:22])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.[Cl-].[Na+].O>[Br:22][CH2:14][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

참가 물질

6

반응물 2

HCID 67184N-bromobutanimideHCID 86723821Methyl 5-ethoxy-2-methylbenzoate

생성물 1

HCID 86723822Methyl 2-(bromomethyl)-5-ethoxybenzoate수율 86.2%

시약·촉매·용매 3

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

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온도
80 °C

실험 절차

To a solution of methyl 5-ethoxy-2-methylbenzoate (134b, 0.700 g, 3.61 mmol) in CCl4 (12 mL) was added BPO (18.0 mg, 0.0720 mmol) and NBS (0.706 g, 3.97 mmol) at room temperature. The resulting mixture was heated at 80° C. for 12 hours under N2 atmosphere. The mixture was diluted with CH2Cl2 (10 mL) and brine (3 mL). The organic layer was separated and washed with NaHCO3 (2 N, 10 mL), H2O (5 mL) and brine (5 mL), dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc=5:1) to give methyl 2-(bromomethyl)-5-ethoxybenzoate (134c, 0.85 g, 86%) as yellow liquid.

후처리

  1. customThe organic layer was separated
  2. washwashed with NaHCO3 (2 N, 10 mL), H2O (5 mL) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography (petroleum ether/EtOAc=5:1)

출처 및 근거

ORD 기록
ord-9039af9cf5a4456791bd97a9e6725b39
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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