Iodine → (2-Hydroxymethylphenyl)acetonitrile

HRID 912039Notes

Reaction equation

HRID 912039 reaction equation
[BH4-].[Na+].[C:3]([CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9])#[N:4].II>C1COCC1>[OH:9][CH2:8][C:7]1[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=1[CH2:5][C:3]#[N:4]

Participants

5

Reactant 3

HCID 807IodineHCID 811142-(Cyanomethyl)benzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 582335(2-Hydroxymethylphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium borohydride (454 mg, 12.0 mmol) in THF (20 mL) was slowly added a solution of 2-cyanomethylbenzoic acid (1.61 g, 10.0 mmol) in THF (20 mL), then a solution of iodine (1.30 g, 5.0 mmol) in THF (20 mL) was slowly added at rt. The resulting mixture was stirred at rt for 1 h. The reaction was quenched with 3 N HCl (10 mL), then extracted with Et2O (3×20 mL). The combined organic phases were washed with brine (20 mL), and dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography (Hex:EtOAc=80:20→60:40) to give the title compound as a yellow oil. 1H NMR (CD3OD): δ=3.98 (s, 2H), 4.27 (s, 2H), 7.33 (m, 2H), 7.41 (m, 2H).

Workup

  1. customThe reaction was quenched with 3 N HCl (10 mL)
  2. extractionextracted with Et2O (3×20 mL)
  3. washThe combined organic phases were washed with brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue was purified by silica gel chromatography (Hex:EtOAc=80:20→60:40)

Sources & evidence

ORD record
ord-dbe063f55fe84fc484ac41209d0646df
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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