Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 58155280, compound

HRID 593340Notes

Reaction equation

HRID 593340 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.F[B-](F)(F)F.[CH3:21][O+](C)C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[N:13]=[C:12]([O:14][CH3:21])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 581553055-(3-Bromophenyl)-5-methylmorpholin-3-one

Product 1

HCID 58155280HCID 58155280, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a vacuum dried flask under an argon atmosphere, a solution of (RS)-5-(3-bromo-phenyl)-5-methyl-morpholin-3-one (3.0 g, 11.1 mmol) in dichloromethane (145 ml) was treated with trimethyloxonium tetrafluoroborate (2.594 g, 17 mmol). The reaction mixture was stirred at room temperature for 17 hours. For the workup, the incomplete reaction was extracted with a saturated solution of sodium hydrogen carbonate (70 ml). The organic layer was dried over sodium sulphate and evaporated. There were obtained 3.12 g of the title compound as a light yellow oil containing about 17% of the starting lactam. Mass (calculated) C12H14BrNO2 [284.16]; (found) [M+H]+=284 and [M+H]+=286.

Workup

  1. customIn a vacuum dried flask under an argon atmosphere
  2. customFor the workup, the incomplete reaction
  3. extractionwas extracted with a saturated solution of sodium hydrogen carbonate (70 ml)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-a4ffb356ce8c4a1db0c808ff2f1e1d88
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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