Pinacol → 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

HRID 2085659Notes

Reaction equation

HRID 2085659 reaction equation
[OH:1][B:2]([OH:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.O[C:14]([C:17](O)([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[CH3:15][C:14]1([CH3:16])[C:17]([CH3:19])([CH3:18])[O:12][B:2]([C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=2)[O:1]1

Participants

4

Reactant 2

HCID 6425PinacolHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-(dihydroxyboryl)benzoic acid (1.66 g, 10 mmol) and pinacol (12 mmol) in toluene (70 mL) was refluxed in a Dean-Stark apparatus for 16 hours and concentrated. The concentrate was triturated with diethyl ether and filtered to provide the desired product of sufficient purity for subsequent use.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was triturated with diethyl ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-87df01e654244ae29ff64a3c47cdb797
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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