Sulfuric Acid → 4-Bromo-2-(2-chloro-1,1-dimethylethyl)anisole

HRID 444076

Reaktionsgleichung

Reaktionsgleichung von HRID 444076
[CH3:1][C:2]([CH2:4][Cl:5])=[CH2:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.S(=O)(=O)(O)O>ClCCl>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([Br:6])=[CH:8][C:9]=1[C:2]([CH3:3])([CH3:1])[CH2:4][Cl:5]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 77304-BromoanisoleHCID 112413-Chloro-2-methyl-1-propene

Produkt 1

HCID 46057784-Bromo-2-(2-chloro-1,1-dimethylethyl)anisoleAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

β-Methallyl chloride (90.5 g, 1.0 mole) was added dropwise to a stirred mixture of p-bromoanisole (200 g, 1.07 mole) and sulphuric acid (34.2 g, 0.35 mole) at 35°-40° C. over about 2 hours. After 21/2 hours at ambient temperature, the mixture was dissolved in dichloromethane, washed with water, aqueous sodium bicarbonate and water again, dried over magnesium sulphate and run down. Distillation of the residue gave a small forerun b.p. about 54° C. at 0.2 mm Hg and a main fraction of 182 g (62%) b.p. 99°-120° C. at 0.15-0.2 mm Hg. Recrystallisation from petroleum ether (b.p. 80°-100° C.) gave 137 g pure title product m.p. 82°-4° C. Reduction in volume of the mother liquors afforded a further 14 g product.

Aufarbeitung

  1. washwashed with water, aqueous sodium bicarbonate and water again
  2. dry with materialdried over magnesium sulphate
  3. distillationDistillation of the residue
  4. customgave a small forerun b.p. about 54° C. at 0.2 mm Hg
  5. customRecrystallisation from petroleum ether (b.p. 80°-100° C.)

Quellen und Nachweise

ORD-Eintrag
ord-d984b1adecf9429c99cf63077136d4a1
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04263037

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