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

HRID 474350Notes

Reaction equation

HRID 474350 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-60e0ed2d14374d01938f396617b354bf
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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