Sodium borohydride → 1-Fluoro-3-(2-nitro-ethyl)-5-propoxy-benzene

HRID 20438Notes

Reaction equation

HRID 20438 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH3:13])[CH:7]=[C:6](/[CH:14]=[CH:15]/[N+:16]([O-:18])=[O:17])[CH:5]=1>C(Cl)(Cl)Cl.C(O)(C)C>[F:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH3:13])[CH:7]=[C:6]([CH2:14][CH2:15][N+:16]([O-:18])=[O:17])[CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 685582311-Fluoro-3-((E)-2-nitro-vinyl)-5-propoxy-benzene

Product 1

HCID 685634311-Fluoro-3-(2-nitro-ethyl)-5-propoxy-benzeneYield 56.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

Add sodium borohydride (1.30 g, 34.46 mmol) to 1-fluoro-3-((E)-2-nitro-vinyl)-5-propoxy-benzene (1.94 g, 8.61 mmol) and silica gel (17 g) in chloroform (86 mL) and isopropanol (25 mL) at room temperature in portions over 5 minutes. Stir at room temperature 2 hours and filter. Concentrate the filtrate and dissolve in ethyl acetate. Wash with water and saturated aqueous sodium chloride, dry over magnesium sulfate, filter and concentrate. Purify on 40 g silica gel eluting with 100:0 to 70:30 hexanes:ethyl acetate to give 1.1 g (56.2%) of the desired compound as an oil.

Workup

  1. filtrationfilter
  2. concentrationConcentrate the filtrate
  3. dissolutiondissolve in ethyl acetate
  4. washWash with water and saturated aqueous sodium chloride
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify on 40 g silica gel eluting with 100:0 to 70:30 hexanes

Sources & evidence

ORD record
ord-8e83b0027be94771977c2a32d98461f9
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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