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

HRID 577594ノート

反応式

HRID 577594 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

HCID 86723822Methyl 2-(bromomethyl)-5-ethoxybenzoate収率 86.2%

試薬・触媒・溶媒 3

HCID 5943Carbon Tetrachloride溶媒HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9039af9cf5a4456791bd97a9e6725b39
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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