4-Bromophenol → 4-(Methoxymethoxy)phenylboronic acid

HRID 2307583Notes

Reaction equation

HRID 2307583 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:11][O:12][CH2:13]Cl.C([Li])CCC.[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C>>[CH3:11][O:12][CH2:13][O:8][C:5]1[CH:6]=[CH:7][C:2]([B:20]([OH:25])[OH:21])=[CH:3][CH:4]=1

Participants

6

Reactant 5

HCID 78084-BromophenolHCID 7864Chloromethyl Methyl EtherHCID 21531Triisopropyl borateHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 27625284-(Methoxymethoxy)phenylboronic acid

Procedure

In a manner similar to that of Example 1(g), by reaction of 10 g (57.8 mmol) of 4-bromophenol with 2.55 g (63.6 mmol) of 60% sodium hydride and 4.83 mL (63.6 mmol) of methoxymethyl chloride, followed by 25.4 mL (63.6 mmol) of 2.5M butyllithium solution and 15 mL (65 mmol) of triisopropyl borate, a brown solid is obtained (m.p.=65° C., m=6.2 g; Y=7.3%).

Workup

  1. customa brown solid is obtained (m.p.=65° C., m=6.2 g; Y=7.3%)

Sources & evidence

ORD record
ord-4fec0d2787644a47afeb21476b5d2af5
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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