1,1'-Carbonyldiimidazole → 2-Fluoro-5-(hydroxymethyl)benzonitrile

HRID 2171351Notes

Reaction equation

HRID 2171351 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[F:12])[C:6](O)=[O:7])#[N:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[BH4-].[Na+]>O1CCCC1>[F:12][C:11]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[C:1]#[N:2]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27739323-Cyano-4-fluorobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 27739342-Fluoro-5-(hydroxymethyl)benzonitrileYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-cyano-4-fluorobenzoic acid (1.00 g, 6.06 mmol) in tetrahydrofuran (THF) (20 mL) was added dropwise CDI (1.47 g, 9.08 mmol) at 0° C. After at room temperature for 30 min, sodium borohydride (0.687 g, 18.2 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 16 h, quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The organic part was separated, dried over Na2SO4, filtered and concentrated. Purification via flash column (petroleum ether/ethyl acetate=10/1) afforded the title product (350 mg).

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. customThe organic part was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash column (petroleum ether/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-bfd939c5df034e318ddb2bc5a3360afa
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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