Potassium Cyanide → 2,4-Difluoro-α-hydroxy-5-methoxybenzeneacetonitrile

HRID 1438149Notes

Reaction equation

HRID 1438149 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[C-:13]#[N:14].[K+].OS([O-])=O.[Na+]>C(OCC)(=O)C.O>[F:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]([OH:5])[C:13]#[N:14]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 23665763Sodium BisulfiteHCID 578038672,4-Difluoro-5-methoxybenzaldehyde

Product 1

HCID 579429112,4-Difluoro-α-hydroxy-5-methoxybenzeneacetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 98A (506 mg, 2.94 mmol) in ethyl acetate (10 mL) was added a solution of KCN (574 mg, 8.82 mmol) and NaHSO3 (917 mg, 8.82 mmol) dissolved in H2O (10 mL). The reaction was stirred at rt for 48 h. It was extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried and concentrated to give 98B as an oil. It was used for next step without purification.

Workup

  1. extractionIt was extracted with ethyl acetate (2×50 mL)
  2. customThe combined organic extracts were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d12308c8358c46069e65ba7d4d129058
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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