Water → (2,6-Dicyanophenyl)boronic acid

HRID 24699

Reaction equation

HRID 24699 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[CH:4]=1)#[N:2].[Li+].CC([N-]C(C)C)C.[B:19](OC)([O:22]C)[O:20]C.O>C1COCC1.CC(O)=O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[C:4]=1[B:19]([OH:22])[OH:20])#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8470Trimethyl borateHCID 12276IsophthalonitrileHCID 2724682Lithium diisopropylamide

Product 1

HCID 22571817(2,6-Dicyanophenyl)boronic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-96 °C

Procedure

1,3-Dicyanobenzene (1.00 g) was dissolved in freshly distilled THF (70 mL). This solution was cooled to −96° C. and LDA (4.2 mL of a 2M solution) was added dropwise to the cold solution under N2. The mixture was stirred for 30 min at −96° C. and (MeO)3B (1.3 mL) was added. The resulting mixture was allowed to warm to room temperature and stirred overnight. Water was added and the resulting mixture was stirred for 0.5 h, then acidified with HOAc and extracted with EtOAc. The organic layer was further washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was taken up in CH2Cl2, filtered and evaporated to yield 2,6-dicyanobenzeneboronic acid (0.56 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. stirringthe resulting mixture was stirred for 0.5 h
  4. extractionextracted with EtOAc
  5. washThe organic layer was further washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-ee26bd4b04f6458fba5b11f5bfdac889
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Linked notes

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