Hydrochloric Acid → 4-Cyano-3,5-dimethylphenylboronic acid

HRID 1714823Notes

Reaction equation

HRID 1714823 reaction equation
C([Li])CCC.Br[C:7]1[CH:14]=[C:13]([CH3:15])[C:10]([C:11]#[N:12])=[C:9]([CH3:16])[CH:8]=1.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.Cl>O1CCCC1>[C:11]([C:10]1[C:13]([CH3:15])=[CH:14][C:7]([B:17]([OH:22])[OH:18])=[CH:8][C:9]=1[CH3:16])#[N:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 109107954-Bromo-2,6-dimethylbenzonitrileHCID 178418339Butyllithium

Product 1

HCID 580862234-Cyano-3,5-dimethylphenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.55 ml of n-butyllithium solution (1.6M in hexane) are added dropwise to a solution of 1.39 g of 4-bromo-2,6-dimethylbenzonitrile in 25 ml of dry tetrahydrofuran at −78° C. After stirring at this temperature for 20 minutes, 1.88 ml of triisopropyl borate are added. After 45 minutes, 15 ml of 1N aqueous HCl are added to the reaction mixture, which is warmed to room temperature. The phases are separated and the aqueous phase is extracted three more times with 100 ml of diethyl ether/tetrahydrofuran (1:1) each time. The combined organic phases are dried with sodium sulphate, filtered and concentrated to 4 ml in vacuo. The remaining oil is mixed with 50 ml of pentane, and the precipitate which has separated out is filtered off with suction and washed twice with pentane. Drying under high vacuum results in the title compound as a beige solid. Rt=3.20.

Workup

  1. waitAfter 45 minutes
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted three more times with 100 ml of diethyl ether/tetrahydrofuran (1:1) each time
  4. dry with materialThe combined organic phases are dried with sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to 4 ml in vacuo
  7. additionThe remaining oil is mixed with 50 ml of pentane
  8. customthe precipitate which has separated out
  9. filtrationis filtered off with suction
  10. washwashed twice with pentane
  11. customDrying under high vacuum

Sources & evidence

ORD record
ord-6079fa41e8d1413f85142413cee8b9b9
Source dataset
uspto-grants-2010_09
Patent number
US07799779B2

Reaction notes

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