Triisopropyl borate → 3-Fluoro-5-(trifluoromethyl)benzeneboronic acid

HRID 989191Notes

Reaction equation

HRID 989191 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:6]([F:8])[CH:7]=1.C([Li])CCC.C([O:21][B:22](OC(C)C)[O:23]C(C)C)(C)C>>[F:8][C:6]1[CH:7]=[C:2]([B:22]([OH:23])[OH:21])[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=1

Participants

4

Reactant 3

HCID 21531Triisopropyl borateHCID 27363233-Bromo-5-fluorobenzotrifluorideHCID 178418339Butyllithium

Product 1

HCID 27831923-Fluoro-5-(trifluoromethyl)benzeneboronic acid

Procedure

3-Bromo-5-fluorobenzotrifluoride was lithiated with n-butyllithium and treated with tri-isopropylborate to give 3-fluoro-5-trifluoromethylphenyl boronic acid. This was coupled to 5-bromopyrimidine, using Suzuki methodology to afford 3-fluoro-5-(pyrimidin-5-yl)benzotrifluoride. Hydrolysis with conc. sulphuric acid and chlorosulphonic acid afforded 3-fluoro-5-(pyrimidin-5-yl)benzoic acid. This was converted to the methyl ester by treatment with methanol and conc. sulphuric acid, and to the hydrazide by treatment with hydrazine hydrate. Diazotisation and treatment with potassium carbonate afforded the title compound.

Sources & evidence

ORD record
ord-0a86916d06dd4d0b8f2e956d3a9f0de8
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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