Triisopropyl borate → 4-(Trifluoromethyl)phenylboronic acid

HRID 1814769Notes

Reaction equation

HRID 1814769 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][CH:4]=1.C([O:15][B:16](OC(C)C)[O:17]C(C)C)(C)C.C([Li])CCC>O1CCCC1>[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([B:16]([OH:17])[OH:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 178418339Butyllithium

Product 1

HCID 27343894-(Trifluoromethyl)phenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of p-trifluoromethylbromobenzene (814.8 g) and triisopropoxyborane (681.0 g) in tetrahydrofuran (6300 mL) is cooled to −78° and n-butyllithium (2.5 m in hexanes, 1448 mL) is added over 30 minutes at a temperature below −60° to yield p-trifluoromethylphenylboronic acid.

Sources & evidence

ORD record
ord-593b3eb93888496eab961284ccdc9173
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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