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

HRID 1785742Notes

Reaction equation

HRID 1785742 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-a3fcb64dbf8e4ca684e97c43bb4fc0a3
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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