Advanced Organic Synthesis. Methods and techniques by Richard S. Monson

By Richard S. Monson

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08 mole), and the flask is heated at 200° (mantle, wax bath, or sand bath) until HBr ceases to be evolved (about 2 hours). -chlorobromobenzene in about 90% yield. Recrystallization from benzene gives the pure product, mp 65-66°. -methoxyphenol (59% yield). III. Allylic and Benzylic Bromination with 7V-Bromosuccinimide As mentioned in an earlier section (cf. Chapter 1, Section III), allylic positions are subject to attack by free radicals resulting in the formation of stable allyl radicals. A^-Bromosuccinimide (NBS) in the presence of free-radical initiators liberates bromine radicals and initiates a chain reaction bromination sequence by the abstraction of allylic or benzylic hydrogens.

7-CHLOROBROMOBENZENE (4) 200° OH + (C 6 Hs) 3 PBr 2 > Cl-/ Q VBr + HBr + (C6H5)3PO Caution: The evolution of HBr in this experiment necessitates the use of a hood or efficient gas trap. 11 mole) of triphenylphosphine dissolved in 100 ml of acetonitrile is converted to triphenylphosphine dibromide. After the addition of the bromine has been completed, the cooling bath is removed, the flask is set up for vacuum distillation, and the solvent is removed. 08 mole), and the flask is heated at 200° (mantle, wax bath, or sand bath) until HBr ceases to be evolved (about 2 hours).

Schaefer, J. G. Higgins, and P. K. Shenov, Org. Syn. 48, 51 (1968). REFERENCES 53 7. C. Djerassi, Chem. Rev. 43, 271 (1948); L. Horner and E. H. Winkelmann in "Newer Methods of Preparative Organic Chemistry" ( W. ), Vol. 3, Academic Press, New York, 1964. 8. N. S. Isaacs, "Experiments in Physical Organic Chemistry," p. 276. Macmillan, London, 1969. 9. F. L. Greenwood and M. D. Kellert, /. Amer. Chem. Soc. 75, 4842 (1953); F. L. Greenwood, M. D. Kellert, and J. Sedlak, Org. Syn. Collective Vol. 4, 108 (1963).

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