Triethylamine → [1,1'-Biphenyl]-3-carbonitrile

HRID 1627960Notes

Reaction equation

HRID 1627960 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN(CC)CC>O.[Cl-].[Na+].O>[C:10]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 233813-BromobenzonitrileHCID 66827Phenylboronic Acid

Product 1

HCID 34340[1,1'-Biphenyl]-3-carbonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-Bromobenzonitrile (91 mg, 0.5 mmol), phenylboronic acid (91 mg, 0.75 mmol), and Pd(dtbpf)Cl2 (6 mg, 0.01 mmol) were added to a reaction tube equipped with a magnetic stir bar. Under a positive flow of argon while stirring, surfactant solution (1.0 mL, 2 wt % TPGS-M-PEG-750 in water), and Et3N (0.21 mL, 1.5 mmol) were added by syringe and stirred vigorously for 2 h. The reaction mixture was then diluted with brine and extracted with EtOAc. The solution obtained was dried over anhydrous MgSO4 and concentrated by rotary evaporation. The residue was purified by flash column chromatography eluting with 20% CH2Cl2/hexanes to afford the product (83 mg, 93%) as a slightly yellow oil.

Workup

  1. customequipped with a magnetic stir bar
  2. stirringstirred vigorously for 2 h
  3. extractionextracted with EtOAc
  4. customThe solution obtained
  5. dry with materialwas dried over anhydrous MgSO4
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 20% CH2Cl2/hexanes

Sources & evidence

ORD record
ord-672f169e9bac4a0c82ccc3ac4420dc73
Source dataset
uspto-grants-2014_07
Patent number
US08785665B2

Reaction notes

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