ChemicalBook CAS DataBase List 2-Bromomethyl-4-cyanophenylboronic acid pinacol ester

2-Bromomethyl-4-cyanophenylboronic acid pinacol ester synthesis

3synthesis methods

Product Name:2-Bromomethyl-4-cyanophenylboronic acid pinacol ester
CAS Number:1030832-26-8
Molecular formula:C14H17BBrNO2
Molecular Weight:322.01

4-Cyano-2-Methylphenylboronic acid, pinacol ester

848953-05-9
49 suppliers
inquiry

2-Bromomethyl-4-cyanophenylboronic acid pinacol ester

1030832-26-8
16 suppliers
inquiry

Yield:1030832-26-8 70%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane; for 53 h;Heating / reflux;

Steps:

13.2

3-Methyl-4- (4, 4, 5, 5-tetramethyl- [ 1, 2, 3] dioxaborolan-2- yl) -benzonitrile (11a, 3.3 g, 0.0136 mol, 1.0 eq) was placed into a 25OmL round-bottom flask containing 50 mL of carbon tetrachloride. NBS (2.5 g, 0.0142 mol, 1.05 equiv.) and catalytic amount of 2, 2 ' -azobisisobutyro- nitrile (0.03 g, 0.00018 mol, 0.014 equiv.) were added and the reaction mixture was refluxed for 53h.The resulting solution was filtered hot then the solvent was removed under vacuum. The crude product was purified by crystallization from hot hexane. Product (12a) containing some 11a was obtained (3.08g, 70%).Structure determination:RP-HPLC Conditions: HP 1100 HPLC chromatograph, 3.9 x 150 mm Symmetry Column HR C18 column, 0.010 mL injection,0.75 mL/min, 1.500 mL injection loop, 254 nm detection, A= water (0.1% TFA) and B = MeCN (0.1% TFA), gradient 10%B 2 min, 10-80% B over 18 min, 80-100% B over 2 min, 100%B 2 min, retention time 13.4 min. ¹H NMR (400 MHz, CDCl₃): δ 1.38 (s, 12H, C(CH₃J₃), 4.85 (s,2H, CH₂Br), 7.55 (d, IH, ArH), 7.68 (s, IH, ArH), 7.92 (d, IH , ArH ) .

References:

WO2008/66921,2008,A2 Location in patent:Page/Page column 48-49

73183-34-3
564 suppliers
$6.00/5g

1030832-26-8
16 suppliers
inquiry

References

41963-20-6
175 suppliers
$15.00/1g

1030832-26-8
16 suppliers
inquiry

References