Bromine → 2-Bromo-3-oxo-3-o-tolyl-propionic acid ethyl ester

HRID 474350ノート

反応式

HRID 474350 の反応式
[Br:1]Br.[CH2:3]([O:5][C:6](=[O:17])[CH2:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[CH3:4]>O1CCOCC1.COC(C)(C)C>[CH2:3]([O:5][C:6](=[O:17])[CH:7]([Br:1])[C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])[CH3:4]

参加物

5

反応物 2

HCID 24408BromineHCID 2760276Ethyl 2-methyl-beta-oxobenzenepropanoate

生成物 1

HCID 224373882-Bromo-3-oxo-3-o-tolyl-propionic acid ethyl ester収率 96.1%

試薬・触媒・溶媒 2

HCID 15413tert-Butyl methyl ether溶媒HCID 312751,4-Dioxane溶媒

実験手順

Bromine (1.65 g, 10.3 mmol, 1.03 equiv) was added drop-wise to a stirred solution of 3-oxo-3-o-tolyl-propionic acid ethyl ester (2.06 g, 10.0 mmol, 1.0 equiv) in 1,4-dioxane (25 mL) at ambient temperature. The mixture was stirred for 1 hour and then diluted with tert-butyl methyl ether (50 mL). The resultant solution was washed sequentially with water, aqueous potassium carbonate solution and saturated aqueous sodium chloride solution. The collected organic was dried over magnesium sulphate, filtered, and concentrated under vacuum to afford 2.74 g (96%) of 2-bromo-3-oxo-3-o-tolyl-propionic acid ethyl ester as a dark brown residue. 1H NMR (400 MHz, CDCl3) δ: 7.66 (d, 1H), 7.46-7.37 (m, 1H), 7.28 (m, 2H), 5.62 (s, 1H), 4.29-4.22 (q, 2H), 2.52 (s, 3H), 1.28-1.19 (t, 3H).

後処理

  1. washThe resultant solution was washed sequentially with water, aqueous potassium carbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialThe collected organic was dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-60e0ed2d14374d01938f396617b354bf
出典データセット
uspto-grants-2014_01
特許番号
US08637526B2

反応ノート

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