Trimethyl borate → 4-Vinylphenylboronic acid

HRID 583647Notes

Reaction equation

HRID 583647 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[Mg].C[O:12][B:13](OC)[O:14]C>C1COCC1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([B:13]([OH:14])[OH:12])=[CH:3][CH:4]=1)=[CH2:7]

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 162634-BromostyreneHCID 5462224Magnesium

Product 1

HCID 27343934-Vinylphenylboronic acidYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure of Example 9 was repeated with the following reagents: 4-bromostyrene (9.15 g, 0.05 mol), magnesium turnings (1.46 g, 0.06 mol), THF (40 mL), and trimethylborate (6.24 g, 0.06 mol in 30 mL of THF). After work-up, an off-white solid (6.9 g, 93 percent) was isolated. 1H and 13C NMR spectra were consistent with the following structure. ##STR13##

Sources & evidence

ORD record
ord-71f47b39369f4e878d8417ed04077aa2
Source dataset
uspto-grants-1999_07
Patent number
US05929194

Reaction notes

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