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

HRID 1977752Notes

Reaction equation

HRID 1977752 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-f979afd4bea440feac2ba3397c9af01b
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

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