N-bromobutanimide → HCID 59282984, compound

HRID 589025Notes

Reaction equation

HRID 589025 reaction equation
[Br:1]N1C(=O)CCC1=O.C([O:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=1)=[CH2:13])C>C1COCC1.O.CCOC(C)=O>[Br:1][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=1)=[O:13]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 90409536HCID 90409536, compound

Product 1

HCID 59282984HCID 59282984, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Bromosuccinimide (200 mg, 1 mmol) was added to a mixture of 2-(1-ethoxyvinyl)-5-fluoropyridine (200 mg, 1 mmol) in THF (6 mL) and water (2 mL). The reaction mixture was stirred at room temperature for 15 min., diluted with EtOAc and washed with brine. The combined organic layer was dried with MgSO4, filtered and concentrated to give 2-bromo-1-(5-fluoropyridin-2-yl)ethanone as a clear oil, which was used in the next step.

Workup

  1. washwashed with brine
  2. dry with materialThe combined organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa2d5660e483471e804cf6aa15b37674
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

Loading…