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

HRID 1436528Notes

Reaction equation

HRID 1436528 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.C(O)(=O)C>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

6

Reactant 3

HCID 176Acetic AcidHCID 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), at room temperature using a water bath to keep the temperature below 35° C. Add acetic acid over 30 min and stir the reaction mixture overnight. Dilute with dichloromethane (660 mL) and wash with 2% aqueous HCl, saturated aqueous sodium chloride, saturated aqueous sodium bicarbonate, dry (magnesium sulfate) and concentrate. Wash the crude with hexanes to give the title compound (220 g).

Workup

  1. customat room temperature
  2. customthe temperature below 35° C
  3. washwash with 2% aqueous HCl, saturated aqueous sodium chloride, saturated aqueous sodium bicarbonate
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. washWash the crude with hexanes

Sources & evidence

ORD record
ord-08eabdce62c345299fcf02685759ec39
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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