2-Nitrobenzoyl chloride → HCID 86718834, compound

HRID 1024332Notes

Reaction equation

HRID 1024332 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[CH3:13][Si:14]([CH3:22])([CH3:21])[C:15]#[C:16][Si](C)(C)C.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](=[O:7])[C:16]#[C:15][Si:14]([CH3:22])([CH3:21])[CH3:13])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 118752-Nitrobenzoyl chlorideHCID 84564Bis(trimethylsilyl)acetyleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86718834HCID 86718834, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
7.5 °C

Procedure

A solution of 2-nitrobenzoyl chloride (13) (225 g; 1.2 moles) and 1,2-bis(trimethylsilyl)ethyne (205 g; 1.2 moles) in dichloromethane (3 L) was cooled to 0° C. Aluminum chloride (159.2 gram, 1.2 moles) was slowly added at 0° C. over 10 minutes while keeping the internal reaction temperature below 10° C. After the addition, the reaction mixture was stirred at 5-10° C. for 1 hour. With stirring, the black reaction mixture was poured into ice-water mixture (2 kg of ice and 1 kg of water). The resulting suspension was filtered and the filter cake was washed with dichloromethane (200 mL). The organic phase of the combined filtrate was separated. The aqueous phase was extracted 2-times with dichloromethane (2×2 L). The combined organic phase was washed with water (2 L), filtered through a Celite pad (200 g), dried over sodium sulfate (120 g), and concentrated at the temperature below 30° C. (bath temperature) to dryness to give 294 g (99% yield) of the desired product in 95% HPLC purity.

Workup

  1. customthe internal reaction temperature below 10° C
  2. additionAfter the addition
  3. stirringWith stirring
  4. filtrationThe resulting suspension was filtered
  5. washthe filter cake was washed with dichloromethane (200 mL)
  6. customThe organic phase of the combined filtrate was separated
  7. extractionThe aqueous phase was extracted
  8. washThe combined organic phase was washed with water (2 L)
  9. filtrationfiltered through a Celite pad (200 g)
  10. dry with materialdried over sodium sulfate (120 g)
  11. concentrationconcentrated at the temperature below 30° C. (bath temperature) to dryness

Sources & evidence

ORD record
ord-5e1c2017966e49c1a7fc42e025be4b63
Source dataset
uspto-grants-2014_05
Patent number
US08722886B1

Reaction notes

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