N-bromobutanimide → HCID 54724200, compound

HRID 1866978Notes

Reaction equation

HRID 1866978 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][N:6]1[C:11]([CH3:12])=[CH:10][C:9]([OH:13])=[CH:8][C:7]1=[O:14].C1C(=O)N([Br:25])C(=O)C1>ClCCl>[Br:25][C:8]1[C:7](=[O:14])[N:6]([CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[C:2]([F:1])[CH:3]=2)[C:11]([CH3:12])=[CH:10][C:9]=1[OH:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54724205HCID 54724205, compound

Product 1

HCID 54724200HCID 54724200, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1-(3-fluorobenzyl)-4-hydroxy-6-methylpyridin-2(1H)-one (0.8 g, 0.0034 mol), NBS (0.64 g, 0.0036 mol) in dichloromethane (15.0 mL) was stirred at room temperature, under argon atmosphere. After 1.5 h, the reaction mixture was diluted with dichloromethane (15.0 mL), cooled and filtered the solids. The residue was washed with dichloromethane and dried in vacuo to give 0.93 g of the title compound as a white powder: 1H-NMR (CD3OD/400 MHz) δ 7.33 (m, 1H), 7.2-6.8 (m, 3H), 6.07 (s, 1H), 5.34 (s, 2H), 2.26 (s, 3H); ESHRMS m/z 312.0016 (M+H C13H12NO2BrF requires 312.0035).

Workup

  1. temperaturecooled
  2. filtrationfiltered the solids
  3. washThe residue was washed with dichloromethane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-50f2c24e5f7447478f5e0b89195e723d
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

Loading…