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Benzoyl Peroxide → Methyl 2-(bromomethyl)-4-(5,6-dimethoxy-3-pyridyl)-6-methylbenzoate

HRID 1259341
ノート
印刷プレビュー

反応式

HRID 1259341 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:20]=[C:19]([CH3:21])[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:22])[CH:12]=2)[CH:6]=[N:7][C:8]=1[O:9][CH3:10].C([O-])([O-])=O.[K+].[K+].C1C(=O)N([Br:36])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:36][CH2:21][C:19]1[CH:20]=[C:11]([C:5]2[CH:6]=[N:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:12]=[C:13]([CH3:22])[C:14]=1[C:15]([O:17][CH3:18])=[O:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7187Benzoyl PeroxideHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 66743002Methyl 4-(5,6-dimethoxy-3-pyridyl)-2,6-dimethylbenzoate

生成物 1

HCID 66743158Methyl 2-(bromomethyl)-4-(5,6-dimethoxy-3-pyridyl)-6-methylbenzoate収率 76.3%

試薬・触媒・溶媒 1

HCID 5943
Carbon Tetrachloride
溶媒

実験手順

As shown in step 6-ii of Scheme 6, Compound 2022 (710 mg, 2.36 mmol) was dissolved in CCl4 (20 mL) and K2CO3 (651 mg, 4.71 mmol), NBS (461 mg, 2.59 mmol), and benzoyl peroxide (57 mg, 0.24 mmol) were added. The reaction mixture was heated to reflux for 4 hours. After cooling to room temperature, the reaction mixture was filtered and the solid washed with CCl4. The filtrate was concentrated to an oil under reduced pressure and purified by silica gel chromatography to provide methyl 2-(bromomethyl)-4-(5,6-dimethoxy-3-pyridyl)-6-methyl-benzoate (Compound 2023, 685 mg, about 70% pure). This compound was used in subsequent reactions as is.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationthe reaction mixture was filtered
  4. washthe solid washed with CCl4
  5. concentrationThe filtrate was concentrated to an oil under reduced pressure
  6. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-59fd9b618f9f4702a65435e8c9c3a0ab
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08466288B2

反応ノート

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