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Trimethyl borate → 3-Fluoro-5-(4-fluorophenoxy)phenylboronic acid

HRID 1078230
Notes
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Reaction equation

HRID 1078230 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:7]=1.C([Li])CCC.[B:22](OC)([O:25]C)[O:23]C>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([B:22]([OH:25])[OH:23])[CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 197072103-Fluoro-5-(4-fluorophenoxy)phenyl bromideHCID 178418339Butyllithium

Product 1

HCID 197072063-Fluoro-5-(4-fluorophenoxy)phenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound is prepared in a manner analogous to that of Step B of Example 6, using 9.1 grams (0.032 mole) of 3-fluoro-5-(4-fluorophenoxy)phenyl bromide, 14 mL (0.035 mole) of n-butyllithium (2.5M in hexanes), and 10.4 mL (0.095 mole) of trimethyl borate in 100 mL of tetrahydrofuran, yielding 3-fluoro-5-(4-fluorophenoxy)phenylboronic acid.

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. customThis compound is prepared in a manner analogous to that of Step B of Example 6

Sources & evidence

ORD record
ord-ea1b1ffeaa6b4e93a6f18d94fbf9366a
Source dataset
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05547954

Reaction notes

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