N-bromobutanimide → Ethyl 6-(bromomethyl)picolinate

HRID 1162583

反応式

HRID 1162583 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)=[O:5])[CH3:2].C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][Br:20])[N:7]=1)=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 564597Ethyl 6-methylpyridine-2-carboxylate

生成物 1

HCID 23033755Ethyl 6-(bromomethyl)picolinate収率 98.3%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 6-methyl-pyridine-2-carboxylic acid ethyl ester (1.65 g, 10 mmol), NBS (1.77 g, 10 mmol), and benzoyl peroxide (100 mg) in carbon tetrachloride (20 ml) was refluxed for 14 h. After cooling to room temperature, the reaction mixture was partitioned between diethyl ether and water (120 ml, 4:1), organic layer was washed with water (2×20 ml), brine, dried (MgSO4), filtered and concentrated to give 6-bromomethyl-pyridine-2-carboxylic acid ethyl ester (2.4 g) which was used without further purification. LCMS m/z: 245 (M+1)+.

後処理

  1. temperaturewas refluxed for 14 h
  2. customthe reaction mixture was partitioned between diethyl ether and water (120 ml, 4:1), organic layer
  3. washwas washed with water (2×20 ml), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-68468710087740078ac5874558b61ab5
出典データセット
uspto-grants-2010_10
特許番号
US07820704B2

関連ノート

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