ChemicalBook CAS DataBase List 9,10-DibromoPhenanthrene

9,10-DibromoPhenanthrene synthesis

7synthesis methods

Product Name:9,10-DibromoPhenanthrene
CAS Number:15810-15-8
Molecular formula:C14H8Br2
Molecular Weight:336.02

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Yield: 91%

Reaction Conditions:

with potassium tert-butylate in N,N-dimethyl-formamide at 0; for 1 h;

Steps:

9,10-Dibromophenanthrene (18).
To a solution of 17 (29.59 g, 59.44 mmol) in anhydrous DMF(450 mL) at 0 °C was added potassium tert-butoxide (21.65 g, 192.9 mmol). The mixture was stirred at 0 °C for 1h, before the mixture was quenched slowly with 6 M HCl (500 mL). The precipitate was filtered, washed with water (1.5 L) and MeOH (200 mL) and dried in vacuo affording 18 as a yellow solid (18.10 g, 91%). The reaction was also done on 3.02 mmol scale giving a yield of 79%. 1H NMR(500 MHz, CDCl3): δ = 8.63 (dd, J = 8.2, 1.4 Hz, 2H), 8.47 (dd, J = 8.1, 1.5 Hz, 2H), 7.70 (ddd, J = 8.2, 7.0,1.5 Hz, 2H), 7.66 (ddd, J = 8.1, 7.0, 1.4 Hz, 2H). 13C NMR (126 MHz, CDCl3): δ = 131.27, 130.36, 129.68,128.18, 127.76, 126.24, 122.84 ppm. HR-MS (APCI+ FT-ICR): m/z = 334.90806 [M+H+], calcd. for[C14H979Br2+]: m/z = 334.90655.

References:

Fernandez, Lorette;Mansø, Mads;Moth-Poulsen, Kasper;Nielsen, Mogens Brøndsted;Wang, Zhihang [Molecules,2020,vol. 25,# 2]