alpha-Bromo-o-fluorotoluene → HCID 18619706, compound

HRID 1862219Notes

Reaction equation

HRID 1862219 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[N:10]2[CH2:11][CH2:12][C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:14][C:9]2=[CH:8][C:7]1=[O:19])=[O:5])[CH3:2].[F:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Br>COCCOC.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O.O>[CH2:1]([O:3][C:4]([CH:6]1[N:10]2[C:11]([CH2:23][C:22]3[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=3[F:20])=[CH:12][C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:14][C:9]2=[CH:8][C:7]1=[O:19])=[O:5])[CH3:2]

Participants

7

Reactant 2

HCID 67968alpha-Bromo-o-fluorotolueneHCID 69707912HCID 69707912, compound

Product 1

HCID 18619706HCID 18619706, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

To 6-ethoxycarbonyl-2-(tert-butyl)-4H-pyrrolo[1,2-a]pyrimid-7-one (0.5 g, 1.9 mmol.) in DME (5 ml), tetrabutylammonium fluoride (4 ml, 4.0M in THF) was added, and a white foamy material formed. 2-Fluorobenzyl bromide (0.38 ml, 3 mmol.) was added and the mixture was stirred at room temperature for 2 days. Concentration of the reaction mixture in vacuo produced an oil, which was dissolved in acetone (20 ml) and diluted with water until the solution turned a slight cloudy. Partially concentration to remove acetone by nitrogen flow resulting precipitation. The precipitates were collected by filtration and washed with water (20 ml×2), ether (20 ml×3) and dried. The desired product (0.57 g) was obtained with excellent purity; MS: 371 (M+H)+, 325; NMR (CDCl3, δ): 8.29 (1H, s), 7.43-7.14(5H, 2m), 5.99 (1H, s) 5.18 (2H,s ), 4.35 (2H, q), 1.37(3H, s), 1.26 (9H, s).

Workup

  1. customa white foamy material formed
  2. customConcentration of the reaction mixture in vacuo produced an oil, which
  3. concentrationPartially concentration
  4. customto remove acetone by nitrogen flow
  5. customresulting
  6. customprecipitation
  7. filtrationThe precipitates were collected by filtration
  8. washwashed with water (20 ml×2), ether (20 ml×3)
  9. customdried

Sources & evidence

ORD record
ord-2b10f92af9c842e9a3b6b474cb88008d
Source dataset
uspto-grants-2003_03
Patent number
US06537998B1

Reaction notes

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