Hydrochloric Acid → B-(4-Cyano-3-ethylphenyl)boronic acid

HRID 1714822Notes

Reaction equation

HRID 1714822 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH2:10][CH3:11])[CH:3]=1.[B:12](OC(C)C)([O:17]C(C)C)[O:13]C(C)C.Cl>CCCCCC.O1CCCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([B:12]([OH:17])[OH:13])=[CH:3][C:4]=1[CH2:10][CH3:11])#[N:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 23023145HCID 23023145, compound

Product 1

HCID 68574647B-(4-Cyano-3-ethylphenyl)boronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

3.66 ml of n-butylithium solution (1.6M in hexane) are added dropwise to a solution of 1.14 g of 4-bromo-2-ethylbenzonitrile in 20 ml of dry tetrahydrofuran at −78° C. After stirring at this temperature for 20 minute, 1.51 ml of triisopropyl borate are added. After 45 minutes, 12 ml of 1N 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 combinred organic phases are dried with sodium sulphate, filtered and concentrated to 4 ml in vacuo. The remainig oil is mixed with 40 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 yellow solid. Rt=3.27.

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 combinred organic phases are dried with sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to 4 ml in vacuo
  7. additionThe remainig oil is mixed with 40 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-6e46f96b849944a5b9f34f7bac594620
Source dataset
uspto-grants-2010_09
Patent number
US07799779B2

Reaction notes

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