N-bromobutanimide → 2-Bromomethyl-3-phenoxy-benzoic acid ethyl ester

HRID 409195Notes

Reaction equation

HRID 409195 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]=1[CH3:18])[CH3:2].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]=1[CH2:18][Br:20])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 671101352-Methyl-3-phenoxy-benzoic acid ethyl ester

Product 1

HCID 671101212-Bromomethyl-3-phenoxy-benzoic acid ethyl esterYield 105.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-methyl-3-phenoxy-benzoic acid ethyl ester (5.23 g, 0.02 mol), N-bromosuccinimide (3.82 g, 0.02 mol) and benzoyl peroxide (247.5 mg, 1.1 mmol) in carbon tetrachloride (80 mL) was refluxed for 4 h before it was cooled to room temperature and filtered. The filtrate was washed with water, saturated aqueous sodium bicarbonate solution, and brine before it was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow oil (7.08 g): 1H NMR (CDCl3, 200 MHz): δ=7.66 (m, 1H), 7.24 (m, 3H), 7.03 (m, 1H), 6.98 (m, 3H), 5.09 (s, 3H), 4.42 (q, J=7.2 Hz, 2H), 1.44 (t, J=7.2 Hz, 3H).

Workup

  1. temperaturewas refluxed for 4 h before it
  2. filtrationfiltered
  3. washThe filtrate was washed with water, saturated aqueous sodium bicarbonate solution, and brine before it
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34329a8e29cd4f9b9c1adcff01833dc3
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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