2-Nitrobenzoyl chloride → HCID 86718834, compound

HRID 1024335Notes

Reaction equation

HRID 1024335 reaction equation
[Cl-].[CH3:2][Si:3]([C:6]#[C:7][Zn+])([CH3:5])[CH3:4].[N+:9]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15])([O-:11])=[O:10].[Cl-].[NH4+]>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:9]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](=[O:15])[C:7]#[C:6][Si:3]([CH3:5])([CH3:4])[CH3:2])([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 118752-Nitrobenzoyl chlorideHCID 25517Ammonium ChlorideHCID 178504288HCID 178504288, compound

Product 1

HCID 86718834HCID 86718834, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The above solution of (trimethylsilyl)ethynyl)zinc(II) chloride (16) in THF was warmed to 0° C., and added to the mixture of 2-nitrobenzoyl chloride (0.94 g) and tetrakis(triphenylphosphine) palladium(0) (176 mg) in tetrahydrofuran at 0° C. under a N2 atmosphere. The reaction mixture was maintained at 0° C. for 30 minutes. Aqueous ammonium chloride solution was added to quench the reaction. It was then extracted 3-times with EtOAc (3×100 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by preparative TLC to give 300 mg of the desired product (11).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionIt was then extracted
  4. dry with materialwith EtOAc (3×100 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-f88a1a2b0dad4435b153fad1ca284946
Source dataset
uspto-grants-2014_05
Patent number
US08722886B1

Reaction notes

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