2-Chloro-4-cyanophenylboronic Acid Pinacol Ester

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2-Chloro-4-cyanophenylboronic Acid Pinacol Ester Basic information
Product Name:2-Chloro-4-cyanophenylboronic Acid Pinacol Ester
Synonyms:2-Chloro-4-cyanophenylboronic Acid Pinacol Ester;3-chloro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile;2-(2-chloro-4-cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Benzonitrile, 3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-carbonitrile;2-Chloro-4-cyanobenzeneboronic acid pinacol ester
CAS:945391-06-0
MF:C13H15BClNO2
MW:263.53
EINECS:
Product Categories:
Mol File:945391-06-0.mol
2-Chloro-4-cyanophenylboronic Acid Pinacol Ester Structure
2-Chloro-4-cyanophenylboronic Acid Pinacol Ester Chemical Properties
Melting point 137.6-143.2 °C
Boiling point 362.8±32.0 °C(Predicted)
density 1.16±0.1 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
AppearanceWhite to light yellow Solid
Safety Information
HS Code 2934999090
MSDS Information
2-Chloro-4-cyanophenylboronic Acid Pinacol Ester Usage And Synthesis
Synthesis
4-Bromo-2-chlorobenzonitrile

154607-01-9

Bis(pinacolato)diboron

73183-34-3

2-Chloro-4-cyanophenylboronic Acid Pinacol Ester

945391-06-0

Bis(pinacolato)diboron (391 mg, 1.54 mmol), potassium acetate (412 mg, 4.5 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (102 mg, 0.14 mmol) were sequentially added to the reaction flask under nitrogen atmosphere. A solution of 2-chloro-4-bromobenzonitrile (300 mg, 1.4 mmol) in dioxane (15 mL) was then added. The reaction mixture was stirred at 80 °C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered through diatomaceous earth and the filter cake was washed with ethyl acetate (50 mL). The filtrate was concentrated under reduced pressure and the resulting residue was purified by preparative thin layer chromatography on silica gel to afford the white solid product 3-chloro-4-pinacolboronate benzonitrile (73 mg, 20% yield). The product was characterized by 1H-NMR (400 MHz, CDCl3): δ 7.78 (d, J = 7.6 Hz, 1H), 7.62 (d, J = 1.2 Hz, 1H), 7.52 (dd, J = 7.6 Hz, 1.2 Hz, 1H), 1.37 (s, 12H) ppm.

References[1] Patent: EP3275867, 2018, A1. Location in patent: Paragraph 0206; 0207
2-Chloro-4-cyanophenylboronic Acid Pinacol Ester Preparation Products And Raw materials
Raw materials4-Bromo-2-chlorobenzonitrile-->Bis(pinacolato)diboron-->1,4-Dioxane-->Potassium Acetate-->[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)
Tag:2-Chloro-4-cyanophenylboronic Acid Pinacol Ester(945391-06-0) Related Product Information
2-Chloro-4-cyanophenylboronic acid 3-Chloro-4-(Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Benzoic Acid 2-Chloro-4-formylphenylboronic acid pinacol ester 2-Chloro-5-cyanophenyl boronic acid pinacol ester Benzonitrile, 2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2-Chlorophenylboronic acid, pinacol ester