Ethanol → 1-Chloro-3-fluoro-5-(2-nitroethyl)benzene

HRID 20360Notes

Reaction equation

HRID 20360 reaction equation
[BH4-].[Na+].C(O)C.[Cl:6][C:7]1[CH:12]=[C:11](/[CH:13]=[CH:14]/[N+:15]([O-:17])=[O:16])[CH:10]=[C:9]([F:18])[CH:8]=1>O1CCOCC1>[Cl:6][C:7]1[CH:12]=[C:11]([CH2:13][CH2:14][N+:15]([O-:17])=[O:16])[CH:10]=[C:9]([F:18])[CH:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 685627261-Chloro-3-fluoro-5-(2-nitroethenyl)benzene

Product 1

HCID 685589231-Chloro-3-fluoro-5-(2-nitroethyl)benzeneYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Add sodium borohydride (0.75 g, 19.7 mmol) to a solution of 1,4-dioxane (10 mL) and absolute ethanol (2.5 mL) in a room temperature water bath. Next add 1-chloro-3-fluoro-5-((E)-2-nitrovinyl)-benzene (1.5 g, 8.98 mmol) in 1,4-dioxane (10 mL) dropwise and stir at room temperature for 1 hour (Bhattacharjya, Synthesis, 1985, 886-997). Add ice chips, glacial acetic acid (2 mL), water (2 mL), concentrate and dilute in dichloromethane/water. Wash the dichloromethane layer with water, saturated aqueous sodium chloride, dry (sodium sulfate), filter and purify (silica gel chromatography, eluting with 1:1 dichloromethane:hexanes) to give the desired compound as an oil (1.07 g 70%).

Workup

  1. custom(Bhattacharjya, Synthesis, 1985, 886-997)
  2. concentrationAdd ice chips, glacial acetic acid (2 mL), water (2 mL), concentrate
  3. additiondilute in dichloromethane/water
  4. washWash the dichloromethane layer with water, saturated aqueous sodium chloride
  5. dry with materialdry (sodium sulfate)
  6. filtrationfilter
  7. custompurify
  8. wash(silica gel chromatography, eluting with 1:1 dichloromethane:hexanes)

Sources & evidence

ORD record
ord-ff19902a0f1c457b80492d632694b4eb
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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