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

HRID 1714819Notes

Reaction equation

HRID 1714819 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][C:10]([CH3:15])=[C:11]([CH:14]=1)[C:12]#[N:13].[B:16](OC(C)C)([O:21]C(C)C)[O:17]C(C)C.Cl>O1CCCC1>[C:12]([C:11]1[CH:14]=[C:7]([B:16]([OH:21])[OH:17])[CH:8]=[CH:9][C:10]=1[CH3:15])#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 129940045-Bromo-2-methylbenzonitrileHCID 178418339Butyllithium

Product 1

HCID 53216722(3-Cyano-4-methylphenyl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.5 ml of n-butyllithium solution (1.6M in hexane) are added dropwise to a solution of 5 g of 5-bromo-2-methylbenzonitrile in 80 ml of dry tetrahydrofuran at −78° C. After stirring at this temperature for 35 minutes, 7.3 ml of triisopropyl borate are added. After one hour, 50 ml of 1N HCl are added to the reaction mixture at −78° C., and the mixture is warmed to room temperature. The phases are separated and the aqueous phase is extracted three more times with 100 ml of diethyl ether each time. The combined organic phases are dried with sodium sulphate, and the solvent is concentrated to 5 ml. The residue is mixed with 150 ml of pentane. The precipitate which has separated out is filtered off with suction and washed twice with pentane. Drying under high vacuum results in 2.85 g of the title compond as a pale yellow solid. Rt=2.98.

Workup

  1. waitAfter one hour
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted three more times with 100 ml of diethyl ether each time
  4. dry with materialThe combined organic phases are dried with sodium sulphate
  5. concentrationthe solvent is concentrated to 5 ml
  6. additionThe residue is mixed with 150 ml of pentane
  7. customThe precipitate which has separated out
  8. filtrationis filtered off with suction
  9. washwashed twice with pentane
  10. customDrying under high vacuum
  11. customresults in 2.85 g of the title compond as a pale yellow solid

Sources & evidence

ORD record
ord-d2fde0ff61eb45739f09ec15f1a9e4ed
Source dataset
uspto-grants-2010_09
Patent number
US07799779B2

Reaction notes

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