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The intermediate 1-bromo-3-chlorocyclobutane can also be prepared via a modified Hunsdiecker reaction from 3-chlorocyclobutanecarboxylic acid using mercuric oxide and bromine: [4] A synthetic approach to bicyclobutane derivatives involves ring closure of a suitably substituted 2-bromo-1-(chloromethyl)cyclopropane with magnesium in THF. [5]
2 Li + C 4 H 9 X → C 4 H 9 Li + LiX where X = Cl, Br. The lithium for this reaction contains 1-3% sodium. When bromobutane is the precursor, the product is a homogeneous solution, consisting of a mixed cluster containing both LiBr and LiBu. 1-Fluorobutane can be obtained by reacting 1-bromobutane with potassium fluoride in ethylene glycol. [5]
All three have been synthesized by various routes: 1-Bromo-2-chlorobenzene: from 2-chloroaniline, via diazotization followed by a Sandmeyer reaction [1]; 1-Bromo-3-chlorobenzene: by (3-chlorophenyl)trimethylgermanium by electrophilic substitution [2] [better source needed]
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Mercuric oxide and bromine convert 3-chlorocyclobutanecarboxylic acid to 1-bromo-3-chlorocyclobutane. This is known as Cristol-Firth modification. This is known as Cristol-Firth modification. [ 14 ] [ 15 ] [ 16 ] The 1,3-dihalocyclobutanes were key precursors to propellanes . [ 17 ]
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"Isomerization of Neopentyl Chloride and Neopentyl Bromide by a 1,2-Interchange of a Halogen Atom and a Methyl Group". The Journal of Physical Chemistry A . 114 (38): 10395– 10402.
2-Bromo-1-chloropropane, C 3 H 6 BrCl, is an alkyl halide. This simple compound has a chiral center and is used sometimes to determine the enantiomeric resolution of simple chromatographic methods. References