ChemicalBook CAS DataBase List 3,5-Dimethylphenylboronic acid

3,5-Dimethylphenylboronic acid synthesis

9synthesis methods

Product Name:3,5-Dimethylphenylboronic acid
CAS Number:172975-69-8
Molecular formula:C8H11BO2
Molecular Weight:149.98

121-43-7
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$13.00/25mL

7732-18-5
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$12.69/100ml

34696-73-6
47 suppliers
$226.00/50mL

172975-69-8
310 suppliers
$9.00/5g

Yield:172975-69-8 74%

Reaction Conditions:

Stage #1:Trimethyl borate;3,5-dimethyphenylmagnesium bromide in tetrahydrofuran at 20;
Stage #2:water with hydrogenchloride in tetrahydrofuran;diethyl ether

Steps:

(3,5-dimethylphenyl)boronic acid
A solution of 3,5-dimethylphenylmagnesium bromide obtained from a solution of190.3 g (1.03 mol) of 1-bromo-3,5-dimethylbenzene in 1000 ml ofTHF and 32 g(1.32 mol, 28% excess) of magnesium turnings was cooled to -78°C, and 104 g (1.0 mol) of trimethylborate was added in one portion. The resulting heterogeneousmixture was stirred overnight at room temperature. The boronic ester washydrolyzed by careful addition of 1200 ml of2 M HCl. 500 ml of diethyl ether wasadded, the organic layer was separated, and the aqueous layer was additionallyextracted with 2 x 500 ml of diethyl ether. The combined organic extract was dried over Na2S04 and then evaporated to dryness to give white mass. The latter wastriturated with 200 ml of hexane, filtered through glass frit (G3), and the precipitatewas dried in vacuo. This procedure gave 114.6 g (74%) of(3,5-dimethylphenyl)boronic acid.Anal. calc. for C8H11B02: C, 64.06; H, 7.39. Found: C, 64.38; H, 7.72. 1H NMR (DMSO-d6): 8 7.38 (s, 2H), 7.00 (s, 1H), 3.44(very br.s, 2H), 2.24 (s, 6H).

References:

BOREALIS AG;AJELLAL, Noureddine;RESCONI, Luigi;IZMER, Vyatcheslav V.;KONONOVICH, Dmitry S.;OSKOBOYNIKOV, Alexander Z.;VIRKKUNEN, Ville WO2018/91684, 2018, A1 Location in patent:Page/Page column 66; 67

FullText

67-56-1 Synthesis