Hydrochloric Acid → 4-Cyanophenylboronic acid

HRID 380968Notes

Reaction equation

HRID 380968 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C([Li])CCC.C([O:18][B:19](OC(C)C)[O:20]C(C)C)(C)C.Cl>O1CCCC1.CCCCCC.[Cl-].[Na+]>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([B:19]([OH:20])[OH:18])=[CH:3][CH:4]=1)#[N:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 12162Benzonitrile, 4-bromo-HCID 21531Triisopropyl borateHCID 178418339Butyllithium

Product 1

HCID 27343264-Cyanophenylboronic acidYield 25%

Reagents, catalysts & solvents 3

HCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 10.0 g (54.9 mmol) of 4-bromobenzonitrile in 100 mL of tetrahydrofuran was cooled to −85° C. wherupon 36.0 mL (57.6 mmol) of 1.6 M solution of n-butyllithium in hexane was added. The mixture was stirred for five minutes and 19.0 mL (82.4 mmol) of triisopropylborate was added. The mixture was stirred at −85° C. for 30 minutes then warmed to ambient temperature over one hour. To the mixture was added 35 mL of 5 N hydrochloric acid and stirring was continued for 2.5 hours. The mixture was diluted with 100 mL of saturated aqueous sodium chloride and extracted three times with 100 mL each of ethyl ether. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was recrystallized from water and filtered to afford 2.0 g (25%) of the title compound.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at −85° C. for 30 minutes
  3. stirringstirring
  4. waitwas continued for 2.5 hours
  5. extractionextracted three times with 100 mL each of ethyl ether
  6. dry with materialThe combined organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from water
  10. filtrationfiltered

Sources & evidence

ORD record
ord-6883008f419c401ab177accf2ae7d828
Source dataset
uspto-grants-2001_10
Patent number
US06303816B1

Reaction notes

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