ChemicalBook CAS DataBase List 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID

3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID synthesis

4synthesis methods

Product Name:3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID
CAS Number:459423-32-6
Molecular formula:C17H23BO3
Molecular Weight:286.17

5419-55-6
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3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID

459423-32-6
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$50.00/25mg

Yield: 94.8%

Reaction Conditions:

Stage #1:2-(1-adamantyl)-4-bromoanisole with n-butyllithium in tetrahydrofuran at -75 - -70; for 1 h;
Stage #2:Triisopropyl borate in tetrahydrofuran at -70 - 20;
Stage #3: with hydrogenchloride;water in tetrahydrofuran at 20;

Steps:

1.a
Example 1 : EPO a) - Preparation of 3-adamantyl-4-mβthoxyphβnylboronic acid (II) :100 g (0.311 mol) of 2- (1-adamantyl) -4-bromoanisole (IV) and 500 ml of THF are introduced, under nitrogen, into a 2 L three-necked reactor. The reaction medium is cooled to -75°C. 137 ml (0.342 mol) of a 2.5 M nBuLi solution are added. After stirring for 1 h at -70⁰C, 80 ml (0.342 mol) of triisopropyl borate are added. After returning to room temperature, the reaction mixture is hydrolysed with 1 litre of 1.2 N HCl. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed with 1 litre of saturated NaCl, and then with 1 litre of water. The organic phases are dried over sodium sulphate and the solvents are evaporated. 88.37 g of a white solid are obtained, which solid is reimpasted in 440 mL of heptane. After filtration, the precipitate obtained is rinsed with heptane, and then dried under reduced pressure at 35°C until a constant weight is obtained. 84.4 g of 3-adamantyl-4-methoxyphenylboronic acid are obtained in the form of a white solid - (yield = 94.8%; m.p. = 263°C) .¹H NMR (CDCl₃): δ: 1.77 (s; 6H); 2.10 (m; 3H); 2.20 (s; 6H); 3.91 (s; 3H); 7.00 (d; IH; J₁₌8.0 Hz); 8.05 (dxd; IH; J₂=I.5 Hz and Ji=8.0 Hz); 8.15 (d; IH, J₂=I.5 Hz)

References:

GALDERMA RESEARCH & DEVELOPMENT, S.N.C. WO2006/108717, 2006, A2 Location in patent:Page/Page column 8-9

104224-63-7 Synthesis