Acetic Anhydride → 1,3-Difluoro-5-(2-nitroethenyl)benzene

HRID 20329Notes

Reaction equation

HRID 20329 reaction equation
C(OC(=O)C)(=O)C.[F:8][C:9]1[CH:10]=[C:11]([CH:16](O)[CH2:17][N+:18]([O-:20])=[O:19])[CH:12]=[C:13]([F:15])[CH:14]=1>CN(C)C1C=CN=CC=1.ClCCl>[F:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][N+:18]([O-:20])=[O:19])[CH:12]=[C:13]([F:15])[CH:14]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 685625531-(3,5-Difluorophenyl)-2-nitroethanol

Product 1

HCID 673487891,3-Difluoro-5-(2-nitroethenyl)benzeneYield 73.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Add acetic anhydride (160 mL) to a solution of 1-(3,5-difluorophenyl)-2-nitroethanol (330 g) and 4-dimethylaminopyridine (18 g) in dichloromethane (1000 mL), over 30 minutes and stir the reaction mixture overnight. Dilute with dichloromethane (600 mL) and wash with 2% aqueous hydrochloric acid, saturated aqueous sodium chloride, saturated aqueous sodium bicarbonate, dry (magnesium sulfate) and concentrate. Wash the crude with hexanes to give the desired compound (220 g).

Workup

  1. washwash with 2% aqueous hydrochloric acid, saturated aqueous sodium chloride, saturated aqueous sodium bicarbonate
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate
  4. washWash the crude with hexanes

Sources & evidence

ORD record
ord-1080cca5ae27486f9ef3c8ea4c9fcc42
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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