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

HRID 1603779Notes

Reaction equation

HRID 1603779 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-5ff1fecb07944059a7f804855c74c8db
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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