Ammonium Chloride → HCID 57514209, compound

HRID 1471435Notes

Reaction equation

HRID 1471435 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[NH4+:12].[Cl-].C[Si]([C:18]#[N:19])(C)C>N>[NH2:12][C:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:11])([CH3:9])[C:18]#[N:19]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 82115Trimethylsilyl cyanideHCID 226074761-(5-Bromo-2-fluorophenyl)ethanone

Product 1

HCID 57514209HCID 57514209, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
30 °C

Procedure

1-(5-Bromo-2-fluorophenyl)-1-ethanone ([CAS 198477-89-3], 65 g, 299.5 mmol) and NH4Cl (32 g, 599 mmol) were dissolved in NH3 (in MeOH, 600 mL). Trimethylsilyl cyanide ([CAS 7677-24-9], 100 g, 1008.6 mmol) was added to the above mixture on an ice bath. The reaction mixture was stirred for 2 days at 30° C. The mixture was evaporated under reduced pressure. The residue was extracted with CH2Cl2 (2×300 mL). The organic layer was collected, dried and evaporated to give the crude product, which was purified by flash column chromatography over silica gel (gradient eluent:ethyl acetate/petrol ether from 1/20 to 1/2). The product fraction was collected and evaporated to give I-11 (60 g, 82%).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. extractionThe residue was extracted with CH2Cl2 (2×300 mL)
  3. customThe organic layer was collected
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-08b274844ef54d7e9b031e96ca5cecf4
Source dataset
uspto-grants-2015_04
Patent number
US09012448B2

Reaction notes

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