Phenol → Phenyl 2-cyanobenzoate

HRID 337449Notes

Reaction equation

HRID 337449 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])#[N:2].[C:12]1(O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:6])#[N:2]

Participants

7

Reactant 4

HCID 996PhenolHCID 8471TriethylamineHCID 1380612-Cyanobenzoic acidHCID 2724699PyBOP

Product 1

HCID 23144259Phenyl 2-cyanobenzoateYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Cyanobenzoic acid (1.00 g, 6.80 mmol), phenol (576 mg, 6.12 mmol) and PyBOP (3.90 g, 7.48 mmol) were dissolved in DMF (12 mL), and triethylamine (2.10 mL, 15.0 mmol) was added thereto, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:2) to afford phenyl 2-cyanobenzoate (1.24 g, 82%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-202f921b15bc4817b2ab3458313e11a7
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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