Benzoyl Peroxide → 1-[4-(Bromomethyl)phenyl]-2,2-dimethylpropan-1-one

HRID 1284203

Reaktionsgleichung

Reaktionsgleichung von HRID 1284203
[C:1]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Br:14]NC(=O)CCC(N)=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 1980932,2-Dimethyl-1-(4-methylphenyl)-1-propanoneHCID 9834204N-Bromosuccinamide

Produkt 1

HCID 128310071-[4-(Bromomethyl)phenyl]-2,2-dimethylpropan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a suspension of 28.5 g. (1.17 g. atoms) magnesium turnings in 150 ml. tetrahydrofuran under a nitrogen atmosphere there is added 10 ml. of 4-bromotoluene (1.17 mole) in 650 ml. dry tetrahydrofuran, the reaction is started and the remainder of the bromotoluene solution is added dropwise at a rate that maintains a moderate reflux. After the addition is complete, the mixture is refluxed for an additional 1 1/2 hours. The resulting Grignard solution is added dropwise to a cold solution of 128.0 g. pivaloyl chloride (1.06 mole) in 500 ml. dry tetrahydrofuran at a rate that maintains the temperature at 0° to -5°C. The solution is stirred for an additional 1 1/2 hours at 0° and then at room temperature for 18 hours. The mixture is then cooled to 0° and hydrolyzed by the addition of 100 ml. 2N hydrochloric acid. The layers are separated and 200 ml. of ether is added to the organic phases which is then washed respectively with 100 ml. 2N hydrochloric acid, 100 ml. 10% sodium bicarbonate solution and 100 ml. saturated sodium chloride. The resulting layer is dried over anhydrous sodium sulfate, filtered, and the solvent is removed in vacuo to give p-pivaloyl toluene (b.p. 80°-84°C./0.7 mm,nD21 1.5108). A mixture of 156.3 g. (0.886 mole) of the resulting p-pivaloyl toluene is then added to 157.8 g. (0.886 mole) N-bromosuccinamide, 4.0 g. (0.016 mole) benzoyl peroxide and 150 ml. carbon tetrachloride and heated at reflux for 18 hours. The mixture is cooled and filtered and the resulting precipitate is washed with carbon tetrachloride. The solvents are removed in vacuo and the resulting oil is distilled in vacuo to give α-bromo-p-pivaloyl toluene (b.p. 124°-132°C./0.7 mm, nD22 1.5546-V.P.C. 96% monobromo 4%-dibromo).

Aufarbeitung

  1. additionA mixture of 156.3 g
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. washthe resulting precipitate is washed with carbon tetrachloride
  6. customThe solvents are removed in vacuo
  7. distillationthe resulting oil is distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4fdbe3c0850043c1b095ff3d2bf7f120
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03978132

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