Acetone → 2-Fluoro-3-(hydroxymethyl)-6-iodobenzonitrile

HRID 1430386Notes

Reaction equation

HRID 1430386 reaction equation
[F:1][C:2]1[C:9]([CH:10]=[O:11])=[CH:8][CH:7]=[C:6]([I:12])[C:3]=1[C:4]#[N:5].[BH4-].[Na+].CC(C)=O>CO>[F:1][C:2]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[C:6]([I:12])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 860193492-Fluoro-3-formyl-6-iodobenzonitrile

Product 1

HCID 666811892-Fluoro-3-(hydroxymethyl)-6-iodobenzonitrileYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 220A (5.0 g, 18 mmol) in MeOH (100 mL) at 0° C. was treated with NaBH4 (822 mg, 22 mmol) and the mixture was stirred for 1 h at 0° C. Acetone was added and the mixture was stirred for 5 min, then concentrated to dryness. The residue was partitioned between H2O and EtOAc. The extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography on silica gel, eluting with 3:2 hexanes/EtOAc to give the desired product (3.14 g). Rf=0.38 (3:2 hexane:EtOAc).

Workup

  1. stirringthe mixture was stirred for 5 min
  2. concentrationconcentrated to dryness
  3. customThe residue was partitioned between H2O and EtOAc
  4. washThe extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluting with 3:2 hexanes/EtOAc

Sources & evidence

ORD record
ord-724ffb4f0cff4f318e0a6c288f678905
Source dataset
uspto-grants-2015_01
Patent number
US08940778B2

Reaction notes

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