Pinacol → 2-[3-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 83560Notes

Reaction equation

HRID 83560 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=1.O[C:13]([C:16](O)([CH3:18])[CH3:17])([CH3:15])[CH3:14].S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)(=O)C>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([B:9]2[O:11][C:16]([CH3:18])([CH3:17])[C:13]([CH3:15])([CH3:14])[O:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6425PinacolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 27732813-(Bromomethyl)benzeneboronic acid

Product 1

HCID 27732832-[3-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 102.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(bromomethyl)phenyl boronic acid (3.13 g) in ethyl acetate (45 ml) were sequentially added pinacol (1.72 g) and anhydrous magnesium sulfate (15 g) at room temperature, and the mixture was stirred for 8 hours. The insoluble substance was filtered off, and the filtrate was concentrated under reduced pressure to give the titled compound (4.43 g).

Workup

  1. customat room temperature
  2. filtrationThe insoluble substance was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5309e3f8643c42de9dd88e346fc3f0e0
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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