Hydrochloric Acid → 1-(2-Chloro-4-fluoro-5-nitrophenyl)ethanone

HRID 636046

Reaction equation

HRID 636046 reaction equation
[Cl-].C[Zn+].[Cl:4][C:5]1[CH:13]=[C:12]([F:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:6]=1[C:7](Cl)=[O:8].Cl.[CH2:19](Cl)Cl>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[Cl:4][C:5]1[CH:13]=[C:12]([F:14])[C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:6]=1[C:7](=[O:8])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 151243842-Chloro-4-fluoro-5-nitrobenzoyl chlorideHCID 178477797HCID 178477797, compound

Product 1

HCID 183144841-(2-Chloro-4-fluoro-5-nitrophenyl)ethanone

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A 2 M solution of methylzinc chloride in tetrahydrofuran (5.00 mL, 10.1 mmol) is treated dropwise with a solution of 2-chloro-4-fluoro-5-nitrobenzoyl chloride (2.00 g, 8.40 mmol) in tetrahydrofuran, treated with tetrakis(triphenylphosphine)palladium(O) (0.400 g, 0.350 mmol), stirred at room temperature for one hour, and poured into 3 N hydrochloric acid. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a dark liquid. Flash column chromatography of the liquid using silica gel and a methylene chloride in hexanes solution (6:4) gives the title product as an off-white solid (mp 66-68° C.) which is identified by NMR spectral analyses.

Workup

  1. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  2. washwashed sequentially with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a dark liquid

Sources & evidence

ORD record
ord-e272d6e23e4c495f94740b8d6e9bcc2f
Source dataset
uspto-grants-2001_02
Patent number
US06191275B1

Linked notes

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