반응 #512334

반응 방정식

4-toluenesulphonamide

sodium hydride

2,3-bis-bromomethyl-1,4-difluorobenzene

→

4,7-difluoro-2-(toluene-4-sulfonyl)isoindoline

수율 56.0%

용매

N,N-dimethylformamide

N,N-dimethylformamide

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도was then cooled to 60° C.
2. 2
   workup.STIRRINGThe mixture was stirred at 60° C. for 1 hour
3. 3
   workup.WAITat room temperature for 16 hours
4. 4
   기타The solvent was removed in vacuo
5. 5
   기타the residue partitioned between dichloromethane and 1M hydrochloric acid
6. 6
   기타The organic layer was separated
7. 7
   세척washed with 5% aqueous potassium carbonate solution
8. 8
   기타the organics were separated
9. 9
   기타the solvent removed in vacuo
10. 10
    세척The residue was rinsed with diethyl ether
11. 11
    여과filtered
12. 12
    기타the solids sucked dry under reduced pressure

실험 절차

A solution of 4-toluenesulphonamide (2.44 g, 14.28 mmol) in N,N-dimethylformamide (10 ml) was added dropwise to a vigorously stirred suspension of sodium hydride (1.2 g, 60 wt % in mineral oil, 30.0 mmol) in anhydrous N,N-dimethylformamide (60 ml). The mixture was stirred at room temperature for 1 hour, at 110° C. for 1 hour and was then cooled to 60° C. and a solution of 2,3-bis-bromomethyl-1,4-difluorobenzene (4.28 g, 14.28 mmol) in N,N-dimethylformamide (30 ml) was added dropwise. The mixture was stirred at 60° C. for 1 hour and then at room temperature for 16 hours. The solvent was removed in vacuo and the residue partitioned between dichloromethane and 1M hydrochloric acid. The organic layer was separated, washed with 5% aqueous potassium carbonate solution, the organics were separated and the solvent removed in vacuo. The residue was rinsed with diethyl ether, filtered and the solids sucked dry under reduced pressure to afford 4,7-difluoro-2-(toluene-4-sulfonyl)isoindoline (2.46 g, 56%) as a pale tan solid. 1H NMR (DMSO-d6) 7.82 (2H, d), 7.43 (2H, d), 7.15 (2H, dd), 4.66 (4H, s), 2.36 (3H, s). MS: [M+H]+ 310.

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