Preparation of 4-bromo-o-xylene in liquid sulfur dioxide

Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing

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570207, 570209, C07C 1712

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050269321

ABSTRACT:
A regioselective process is provided for preparing 4-bromo-o-xylene in an isomer mixture of 4-bromo-o-xylene and 3-bromo-o-xylene by combining bromine with o-xylene in liquid sulfur dioxide medium. A bromine to o-xylene mole ratio of about 0.4:1 to about 1:1 is utilized at a temperature in the range of about -20.degree. C. to about 40.degree. C. While preferred temperatures are in the about -15.degree. C. to about -9.degree. C. range, temperatures above about -9.degree. C. can be used by maintaining the reactant solution under pressure. A product isomer mixture can be isolated by vacuum distillation. A 92:8 weight ratio mixture of 4-bromo-o-xylene and 3-bromo-o-xylene is thus obtainable.

REFERENCES:
patent: 2452154 (1948-10-01), Ross
patent: 3932542 (1976-06-01), Gerns
Meirovics et al., "Chemical Abstracts" vol. 74 (1971) 42032v.
Canselier, Bull. Soc. Chim. France (1972) pp. 762-764.
Canselier, Bull. Soc. Chim. France (1971) pp. 1785 and 1788.

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