Potassium Carbonate → [4-[(2-Cyanobenzyl)thio]phenyl]boronic acid

HRID 452639Notes

Reaction equation

HRID 452639 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1.Br[CH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:15]([C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[CH2:12][S:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1)#[N:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 895992-(Bromomethyl)benzonitrileHCID 44318944-Mercaptophenylboronic acid

Product 1

HCID 68663291[4-[(2-Cyanobenzyl)thio]phenyl]boronic acidYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of (4-mercaptophenyl)boronic acid (0.847 g, 5.50 mmol), 2-(bromomethyl)benzonitrile (1.62 g, 8.25 mmol) and potassium carbonate (2.28 g, 16.5 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with hexane/ethyl acetate (2/1) and recrystallized from hexane/ethyl acetate to give the title compound (903 mg, yield 61%) as colorless crystals.

Workup

  1. washwashed twice with water and once with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was washed with hexane/ethyl acetate (2/1)
  5. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-739e314a2ef840139373c15a60e9b468
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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