Hydrochloric Acid → (3-Cyano-4-isobutoxyphenyl)boronic acid

HRID 562886Notes

Reaction equation

HRID 562886 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[C:6]([CH:9]=1)[C:7]#[N:8].[B:15](OC(C)C)([O:20]C(C)C)[O:16]C(C)C.Cl>C1COCC1.C1(C)C=CC=CC=1>[C:7]([C:6]1[CH:9]=[C:2]([B:15]([OH:20])[OH:16])[CH:3]=[CH:4][C:5]=1[O:10][CH2:11][CH:12]([CH3:14])[CH3:13])#[N:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 665851345-Bromo-2-isobutoxybenzonitrile

Product 1

HCID 54576546(3-Cyano-4-isobutoxyphenyl)boronic acid

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-2-isobutoxybenzonitrile and triisopropyl borate were dissolved in a mixed solvent of THF and toluene and an n-butyllithium-hexane solution was added dropwise to the solution at a temperature below −60° C. After the temperature was elevated to −20° C., 1M hydrochloric acid was added, followed by stirring at room temperature to obtain (3-cyano-4-isobutoxyphenyl)boronic acid. F: 220.

Workup

  1. additionan n-butyllithium-hexane solution was added dropwise to the solution at a temperature below −60° C
  2. customwas elevated to −20° C.

Sources & evidence

ORD record
ord-3c37fd9fc19e46d68083b3266a4d7705
Source dataset
uspto-grants-2011_11
Patent number
US08067446B2

Reaction notes

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