Kharasch, M. S.'s team published research in Journal of Organic Chemistry in 20

Kharasch, M. S. published the artcileVapor-phase photochemical bromination of 2,3-dimethylbutane and 2,2,4,4-tetramethylpentane, Category: bromides-buliding-blocks, the publication is Journal of Organic Chemistry (1955), 680-8, database is CAplus.

cf. C.A. 50, 173e. The vapor-phase, photochem. bromination of 700 g. (CHMe₂)₂ (I) with 360 g. Br is carried out in the apparatus described earlier (cf. Zimmt, Dissertation, Univ. of Chicago, 1951). After 10 h. the bromination products are stripped of HBr with N and the residue is fractionally distilled, giving 35% 2-bromo-2,3-dimethylbutane, b_27.5 41-1.5°, n_D²⁰ 1.4541. Cooling the distillation residue gives 4% (CBrMe₂)₂, subliming 170-5° without melting. High-vacuum distillation of the high-boiling residue gives 3 fractions: (a) 46 g., b_0.2 44-6°; (b) 5.4 g., b_0.2 67-70°; (c) 10.1 g., b_0.4 96-100°. Redistillation of a gives 25% of a mixture of cis- and trans-(:CMeCH₂Br)₂, b_0.1 40°, needles, m. 57-7.5°; b is a mixture of tri- and tetrabromides and is not investigated further; recrystallization of c gives 5% tetrabromide, needles, m. 149-52°, of unknown structure. Treating 2 g. of a in 25 cc. CCl₄ with 1.5 g. Br 40 min. at 20° with moderate illumination gives 1.8 g. (CBrMeCH₂Br)₂, faintly yellow needles, m. 137-8°. Because little or no bromination of 2,2,4,4-tetramethylpentane (II) occurs in the vapor phase photochem. bromination at 100° and because of the limited amount of II available a special apparatus, similar to that for I, is used. The bromination of 27 g. II with 14 g. Br is carried out over a period of 7.5 h. at 200°. The reaction product is freed of Br and HBr with N and fractionally distilled in vacuo giving 3 fractions: (d) 0.7 g., b₅ 51°, n_D²⁰ 1.4690; (e) 1.1 g., b₅ 51-2°, n_D²⁰ 1.4695; (f) 11.2 g., b₅ 52°, n_D²⁰ 1.4719; and 0.6 g. residue, apparently a dibromide. The total yield of d-f is 72.2% and is shown to be 2-bromo-2,3,4,4-tetramethylpentane (III). Treating f 0.5 h. with AgNO₃ gives 92.5% AgBr. Shaking 2.1 g. f with 2 g. AgOAc in 30 cc. AcOH and 0.3 cc. Ac₂O 1 h. and distilling off the solvent in vacuo leave 0.5 g. residue which gives a pos. hydroxamic acid test for esters. Neutralizing the distillate with Na₂CO₃, extracting with Et₂O, and evaporating the extract leave 0.6 g. unsaturated material which, on ozonization, gives HCHO. Shaking 2.07 g. f in 45 cc. anhydrous Et₂O with 7.3 g. 3,4-(O₂N)₂C₆H₃CO₂Ag 36 h. gives 2,3,4,4-tetramethylpent-1-ene, b₇₅₄ 125-6°, n_D²⁰ 1.4261, which (0.1 g.), ozonized in 100 cc. EtOAc 2.5 min. at -40°, gives 3,4,4-trimethylpentan-2-one identified via its 2,4-dinitrophenylhydrazone, orange needles, m. 109-10°. III is formed by rearrangement of a Me group. Mechanisms which account for the formation of mono- and dibromides with free radicals as intermediates are proposed.

Journal of Organic Chemistry published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C6H12Br2, Category: bromides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary