Propylene Oxide → HCID 65490426, compound

HRID 2200133Notes

Reaction equation

HRID 2200133 reaction equation
[CH2:1]1[O:4][CH:2]1[CH3:3].Cl([O-])(=O)(=O)=O.[Li+].[Br:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[NH2:15]>C(#N)C>[Br:11][C:12]1[CH:13]=[C:14]([NH:15][CH2:1][CH:2]([OH:4])[CH3:3])[CH:16]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:18]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 27358803-Bromo-5-(trifluoromethyl)anilineHCID 23665649Lithium perchlorate

Product 1

HCID 65490426HCID 65490426, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add propylene oxide (36 mg, 0.624 mmol) and lithium perchlorate (56 mg, 0.458 mmol) to the solution of 3-bromo-5-(trifluoromethyl)aniline (100 mg, 0.416 mmol) in acetonitrile (5 mL), stir the resulting mixture overnight at ambient temperature. Upon completion of the reaction, concentrate the mixture under reduced pressure. Purify the residue by flash chromatography (silica gel, PE:EtOAc=5:1) to afford the product (136 mg, 100%).

Workup

  1. customUpon completion of the reaction
  2. concentrationconcentrate the mixture under reduced pressure
  3. customPurify the residue by flash chromatography (silica gel, PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-7d860c99f28b4a678e3f610301e999ff
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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