Hydrochloric Acid → 3-Cyanophenylboronic acid

HRID 551266Notes

Reaction equation

HRID 551266 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[B:10](OC(C)C)([O:15]C(C)C)[O:11]C(C)C.C([Li])CCC.CCCCCC.Cl>C1COCC1>[C:5]([C:4]1[CH:3]=[C:2]([B:10]([OH:15])[OH:11])[CH:9]=[CH:8][CH:7]=1)#[N:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 21531Triisopropyl borateHCID 233813-BromobenzonitrileHCID 178418339Butyllithium

Product 1

HCID 27343253-Cyanophenylboronic acidYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-Bromobenzonitrile (3.6 g, 20 mmol) in anhydrous THF (100 ml) is treated with triisopropyl borate (13 ml, 56 mmol) followed by 1.6 M butyllithium in hexane (14 ml, 22 mmol) over 15 min. at −78° C. The reaction is stirred at −78° C. for 45 min . then warmed to room temperature over 60 min. The reaction mixture is poured into 40 ml 2 N HCl and the precipitated solid is collected . The filter cake is washed with water (3×) and methylene chloride (3×) to yield 3-cyanophenyl boronic acid (2.3 g, 15.6 mmol). 1H NMR (CDCl3, 300 MHz) δ 8.4 (br, 2H), 8.13 (s, 1H), 8.07 (d, 1H), 7.85 (d, 1H), 7.55 (t, 1H). EI MS M+ 147.

Workup

  1. temperaturethen warmed to room temperature over 60 min
  2. customthe precipitated solid is collected
  3. washThe filter cake is washed with water (3×) and methylene chloride (3×)

Sources & evidence

ORD record
ord-3260fdbb1b5f4012a204cc57c77f46dd
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

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