Pinacol → 3-Chloropropenyl-1-boronic acid pinacol ester

HRID 1853926Notes

Reaction equation

HRID 1853926 reaction equation
[Cl:1][CH2:2]/[CH:3]=[CH:4]/[B:5]([OH:7])[OH:6].O[C:9]([C:12](O)([CH3:14])[CH3:13])([CH3:11])[CH3:10].S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[Cl:1][CH2:2]/[CH:3]=[CH:4]/[B:5]1[O:7][C:12]([CH3:14])([CH3:13])[C:9]([CH3:11])([CH3:10])[O:6]1

Participants

5

Reactant 3

HCID 6425PinacolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 6080110B-[(1E)-3-Chloro-1-propen-1-yl]boronic acid

Product 1

HCID 118305003-Chloropropenyl-1-boronic acid pinacol esterYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-3-chloroprop-1-enylboronic acid (5 g, 41 mmol), pinacol (4.9 g, 41 mmol), and magnesium sulfate (15 g, 120 mmol) in methylene chloride (100 mL) was stirred at room temperature for 18 h. The reaction mixture was filtered through silica gel and the filter cake was washed with methylene chloride. The filtrate was concentrated to afford the desired product (4.8 g, 60%) as a colorless oil: ESI MS m/z 203 [C9H16BClO2+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through silica gel
  2. washthe filter cake was washed with methylene chloride
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b6f8ebc4cc6a4d118f83508cf7823cbd
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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