2-Iodophenol → 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C1([B:15]2[O:23][C:20]([CH3:22])([CH3:21])[C:17]([CH3:19])([CH3:18])[O:16]2)C=CC=CC=1>>[CH3:18][C:17]1([CH3:19])[C:20]([CH3:22])([CH3:21])[O:23][B:15]([C:7]2[CH:2]=[C:3]([OH:8])[CH:4]=[CH:5][CH:6]=2)[O:16]1

Participants

Reactant 2

HCID 107842-Iodophenol2×

HCID 570673Phenylboronic acid pinacol ester

Product 1

HCID 27346233-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Procedure

The above reaction procedure used for 2-iodophenol was followed. The reaction was faster, being complete before the first sample for gc analysis was withdrawn after 1 h 50 min reaction time. The amount of phenylboronic acid pinacol ester was higher than in the 2-iodophenol reaction (around 7%).

Workup

customThe above reaction procedure
customwas withdrawn after 1 h 50 min
customreaction time

Sources & evidence

ORD record: ord-23004de992854d06895bd83361499298
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122694B2

Reaction notes

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