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

HRID 474350노트

반응식

HRID 474350 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 15413tert-Butyl methyl ether용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-60e0ed2d14374d01938f396617b354bf
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637526B2

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