Benzoyl Peroxide → HCID 68632004, compound

HRID 1809469Notes

Reaction equation

HRID 1809469 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1C(=O)N([Br:21])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:13][Br:21])=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68633230methyl 3-bromo-5-fluoro-2-methylbenzoate

Product 1

HCID 68632004HCID 68632004, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of (E4), NBS (1.2 eq.) and benzoyl peroxide (0.1 eq.) in CCl4 (0.28 M) was heated to reflux for 4.5 h. Afterwards, the reaction mixture was cooled down to 0° C. and the solid filtered off. The solid was washed with Et2O and the filtrate was washed sequentially with 1 M Na2S2O3, brine and dried (Na2SO4). Evaporation of the solvent under reduced pressure afforded the title compound that was used without further purification in the next step. 1H NMR (400 MHz, CDCl3, 300 K) δ 7.63 (1H, dd, J=8.6 and 2.8 Hz), 7.52 (1H, dd, J=7.4 and 2.8 Hz), 5.10 (2H, s), 3.97 (3H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 h
  3. filtrationthe solid filtered off
  4. washThe solid was washed with Et2O
  5. washthe filtrate was washed sequentially with 1 M Na2S2O3, brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ed7b6d142d744fc8a1e78924a64e69ba
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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