Benzoyl Peroxide → Biphenyl-4-yl-bromo-acetic acid methyl ester

HRID 539848Notes

Reaction equation

HRID 539848 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CC#N.O>C(Cl)(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)[Br:18]

Participants

7

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 30808634-Biphenylylacetic acid methyl esterHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 11822880Biphenyl-4-yl-bromo-acetic acid methyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of biphenyl-4-yl-acetic acid methyl ester (5 g., 22.1 mmol) in carbon tetrachloride (from Acros, 16772) (25 mL) was added N-bromosuccinimide (from Aldrich, 18350) (3.9 g., 22.1 mmol) and benzoyl peroxide (from Acros, 21178) (0.54 g, 2.2 mmol) and the reaction was heated to reflux for 48 hours. The reaction mixture was cooled to room temperature, filtered and the filtrate concentrated in vacuo to afford Cpd. 2 as a crude yellow oil (6.24 g., 93% yield). 1HNMR (CDCl3) δH, 3.81, 3H (s, CH3), 5.41, 1H (s, Br—CH), 7.33-7.39, 2H (m, Ar—H), 7.41-7.46, 3H (m, Ar—H), 7.54-7.63, 4H (m, Ar—H); LCMS analysis (solvent MeCN/H2O/0.1% HCO2H, 5-95% gradient/H2O 2.5 min, 95% 4 min., Phenomenex C18 reverse phase, flow rate 1 mL/min.) HPLC retention time 4.39 min.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 48 hours
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customto afford Cpd

Sources & evidence

ORD record
ord-2b653551695c4e319803072aed7ec319
Source dataset
uspto-grants-2014_10
Patent number
US08871772B2

Reaction notes

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