Pinacol → 2-(2-Fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 2406380Notes

Reaction equation

HRID 2406380 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[B:9]([OH:11])[OH:10].O[C:13]([C:16](O)([CH3:18])[CH3:17])([CH3:15])[CH3:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[B:9]1[O:10][C:16]([CH3:18])([CH3:17])[C:13]([CH3:15])([CH3:14])[O:11]1

Participants

5

Reactant 3

HCID 6425PinacolHCID 521998p-Toluenesulfonic acid monohydrateHCID 2783132(2-Fluoro-4-methylphenyl)boronic acid

Product 1

HCID 696724352-(2-Fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (2-fluoro-4-methylphenyl)boronic acid (500 mg, 3.24 mmol) in diethyl ether (20 mL) was added pinacol (360 mg, 3.24 mmol) and 4-toluenesulfonic acid monohydrate (30 mg, 162 μmol) and the resulting solution was stirred at room temperature for 18 hours. The reaction mixture was washed with a saturated aqueous sodium hydrogen carbonate solution (20 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a white solid, 740 mg, in a 97% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.33 (s, 12H), 2.34 (s, 3H), 6.82 (d, 1H), 6.93 (d, 1H), 7.60 (d, 1H).

Workup

  1. washThe reaction mixture was washed with a saturated aqueous sodium hydrogen carbonate solution (20 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ae46c4cdaf6403081e119dca1cae9b2
Source dataset
uspto-grants-2014_08
Patent number
US08809363B2

Reaction notes

Loading…