![](/CAS/GIF/172975-69-8.gif)
3,5-Dimethylphenylboronic acid synthesis
- Product Name:3,5-Dimethylphenylboronic acid
- CAS Number:172975-69-8
- Molecular formula:C8H11BO2
- Molecular Weight:149.98
![Trimethyl borate](/CAS/GIF/121-43-7.gif)
121-43-7
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![Water](/CAS/GIF/7732-18-5.gif)
7732-18-5
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$12.69/100ml
![3,5-DIMETHYLPHENYLMAGNESIUM BROMIDE](/CAS/GIF/34696-73-6.gif)
34696-73-6
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$226.00/50mL
![3,5-Dimethylphenylboronic acid](/CAS/GIF/172975-69-8.gif)
172975-69-8
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$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
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67-56-1
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![BORANE-DIISOPROPYLAMINE](/CAS/20211123/GIF/55124-35-1.gif)
55124-35-1
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$60.00/100mg
![5-Bromo-m-xylene](/CAS/GIF/556-96-7.gif)
556-96-7
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$6.00/5g
![3,5-Dimethylphenylboronic acid](/CAS/GIF/172975-69-8.gif)
172975-69-8
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$9.00/5g
![5-Bromo-m-xylene](/CAS/GIF/556-96-7.gif)
556-96-7
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![3,5-Dimethylphenylboronic acid](/CAS/GIF/172975-69-8.gif)
172975-69-8
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$9.00/5g
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5419-55-6
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![5-Bromo-m-xylene](/CAS/GIF/556-96-7.gif)
556-96-7
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$6.00/5g
![3,5-Dimethylphenylboronic acid](/CAS/GIF/172975-69-8.gif)
172975-69-8
313 suppliers
$9.00/5g
![Trimethyl borate](/CAS/GIF/121-43-7.gif)
121-43-7
344 suppliers
$13.00/25mL
![5-Bromo-m-xylene](/CAS/GIF/556-96-7.gif)
556-96-7
377 suppliers
$6.00/5g
![3,5-Dimethylphenylboronic acid](/CAS/GIF/172975-69-8.gif)
172975-69-8
313 suppliers
$9.00/5g