Pinacol → 5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

HRID 63943Notes

Reaction equation

HRID 63943 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[C:4]([OH:11])[CH:3]=1.O[C:13]([C:16](O)([CH3:18])[CH3:17])([CH3:15])[CH3:14]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]2[O:9][C:16]([CH3:18])([CH3:17])[C:13]([CH3:15])([CH3:14])[O:10]2)=[C:4]([OH:11])[CH:3]=1

Participants

4

Reactant 2

HCID 6425PinacolHCID 67464855B-(4-Chloro-2-hydroxyphenyl)boronic acid

Product 1

HCID 676093145-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-chloro-2-hydroxyphenyl)boronic acid (Preparation 15, 200 mg, 1.16 mmol) in dichloromethane (15 mL) was added pinacol (274 mg, 2.32 mmol) and the resulting solution was stirred at room temperature for 18 hours. The reaction mixture was washed with water (10 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound as a pale yellow solid, 280 mg, in a 95% yield.

Workup

  1. washThe reaction mixture was washed with water (10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53f8e11e0fcf4d0dbd815bb0f8eebd02
Source dataset
uspto-grants-2016_09
Patent number
US09447116B2

Reaction notes

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