ChemicalBook CAS DataBase List 2-METHOXYPHENYLBORONIC ACID PINACOL ESTER

2-METHOXYPHENYLBORONIC ACID PINACOL ESTER synthesis

13synthesis methods

Product Name:2-METHOXYPHENYLBORONIC ACID PINACOL ESTER
CAS Number:190788-60-4
Molecular formula:C13H19BO3
Molecular Weight:234.1

76-09-5 Synthesis

76-09-5
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22092-92-8
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2-methoxybenzenediazonium tetrafluoroborate

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2-METHOXYPHENYLBORONIC ACID PINACOL ESTER

190788-60-4
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Yield: 69%

Reaction Conditions:

Stage #1:diisopropopylaminoborane;2-methoxyphenyldiazonium tetrafluoroborate with ferrocene in acetonitrile at 20; for 2.5 h;
Stage #2: with methanol in acetonitrile at 0 - 20; for 1 h;
Stage #3:2,3-dimethyl-2,3-butane diol in diethyl ether;acetonitrile at 20; for 4 h;Reagent/catalyst;

Steps:

5 Example 5: synthesis of 2-( -methoxyphenyr)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane [CAS 190788-60-41], compound VI_A2
Example 3: General procedure D for the synthesis of the arylpinacolboronates by arylation of diisopropylaminoborane, catalysed by ferrocene (1%), followed by methanolysis and transesterification In a dried tube reactor under argon as described in example 2, the arenediazonium salt (1 mmol) and the ferrocene (ΙΟμιηοΙ, 1.8mg) were dissolved in 2mL of anhydrous CH₃CN. Diz^'sopropylaminoborane (2mmol, 226mg) was then added to the solution and the mixture was stirred for 2h30 at room temperature. The reaction mixture was quenched by a slow addition of anhydrous MeOH at 0°C (2mL) and stirred for an additional hour at room temperature. After removal of all the volatiles, 1.3eq of pinacol was added in Et₂0 (2mL), the mixture was stirred 4h at room temperature. The crude mixture was washed with a 50g/L CuCl₂ solution (2 x 5mL). The organic layer were separated, dried over Na₂S0₄, filtered and concentrated to dryness. The resulted oil was dissolved with CH₂C1₂ and filtered of a pad of silica gel, eluting with CH₂C1₂ to afford the corresponding boronate. Example 5: synthesis of 2-( -methoxyphenyr)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane iCAS 190788-60-41, compound VI 161 mg of 2-(l-methoxyphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane were obtained following the general procedure D according to example 3, using 222 mg of 2- methoxybenzenediazonium tetrafluoroborate as a pale yellow oil, with an isolated yield of 69%. 1H NMR (300 MHz, CDC1₃) δ 7.67 (dd, J = 7.3, 1.8 Hz, 1H), 7.39 (ddd, J = 8.5, 7.5, 1.9 Hz, 1H), 6.94 (t, J = 7.3 Hz, 1H), 6.86 (d, J = 8.4 Hz, 1H), 3.83 (s, 3H), 1.36 (s, 12H) nB NMR (100 MHz, CDC1₃) δ 31.09 ¹³C NMR (75 MHz, CDC1₃) δ 136.69, 132.43, 120.21, 110.51, 83.45, 55.84, 24.84

References:

UNIVERSITE DE BORDEAUX 1;CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE;PUCHEAULT, Mathieu Jonathan Damien;MARCIASINI, Ludovic Daniel Alain;VAULTIER, Michel WO2014/9169, 2014, A1 Location in patent:Page/Page column 54-55