ChemicalBook CAS DataBase List 1,3-Dibromonaphthalene

1,3-Dibromonaphthalene synthesis

5synthesis methods

Product Name:1,3-Dibromonaphthalene
CAS Number:52358-73-3
Molecular formula:C10H6Br2
Molecular Weight:285.96

Naphthalene, 1,2,3,4-tetrabromo-1,2,3,4-tetrahydro-

19922-78-2
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52358-73-3
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Yield:52358-73-3 88%

Reaction Conditions:

with potassium tert-butylate in tetrahydrofuran at 20;

Steps:

1,3-dibromonaphthalene 5
1,2,3,4-tetrabromo-1,2,3,4-tetrahydronaphthalene (3.0 g, 6.7 mmol, 1 eq.) in 27 ml of dry THF was added to the suspension of potassium tert-butoxide (1.9 g, 16.7 mml, 2.5 eq.) in dry THF (8 ml). The reaction mixture was stirred at r.t. overnight. Next day water was added to the mixture and the mixture was extracted with diethyl ether three times, dried over MgSO₄ and evaporated to dryness. The residue was filtered through a short silica column using light petroleum (bp = 40 - 60°C) as an eluent. Product (1.69 g, 88 %) was obtained as a colourless oil that solidified upon freezing (-20°C). The spectroscopic data were consistent with that previously reported.^{1, 2 1}H NMR (400 MHz, CD₂Cl₂) δ 8.20 (d, J = 8.3 Hz, 1H, H-8), 8.02 (d, J = 1.9 Hz, 1H, H-4), 7.91 (d, J = 1.9 Hz, 1H, H-2), 7.79 (dd, J = 8.2, 1.5 Hz, 1H, H-5), 7.66 - 7.56 (m, 2H, H-6,7). ¹³C NMR (101 MHz, CD₂Cl₂) δ 135.7 (C-4a), 133.1 (C-2), 131.2 (C-8a), 130.6 (C-4), 128.4 (C-7), 128.4 (C-6), 128.1 (C-5), 127.6 (C-8), 123.9 (C-1), 119.3 (C-3).

References:

Turunen, Lotta;Németh, Flóra Boróka;Decato, Daniel A.;Pápai, Imre;Berryman, Orion B.;Erdélyi, Máté [Bulletin of the Chemical Society of Japan,2021,vol. 94,# 1,p. 191 - 196] Location in patent:supporting information

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91-20-3 Synthesis