Reaction equation
S(=O)(=O)(O)[OH:2].[Br:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[NH:14][C:15](=[O:19])[CH:16]=NO>CCOC(C)=O>[Br:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]2[C:8]=1[NH:14][C:15](=[O:19])[C:16]2=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A 2 L 3-neck flask with a temperature probe adapter was fixed with a mechanical stirrer, condenser, and temperature probe. The flask was charged with conc. sulfuric acid (79 mL, 1418 mmol) and was heated to 70° C.; solid N-(2-bromo-3-fluorophenyl)-2-(hydroxyimino)acetamide (719a; 12.34 g, 47.3 mmol) was then slowly added (exotherm) and the temperature raised to 100° C. The brown solution was stirred at 90° C. for 45 min. The heating mantle was replaced with an ice bath to cool the reaction mixture to RT; the brown solution was poured into a beaker containing ice (500 mL), diluted with EtOAc (200 mL), added to a separatory funnel, and extracted with EtOAc (2×150 mL); the combined organics were dried over Na2SO4 and concentrated to give 7-bromo-6-fluoroindoline-2,3-dione (11.53 g, 47.3 mmol, 100% yield) as a reddish solid. 1H NMR (400 MHz, CDCl3) δ ppm 6.91 (t, J=8.51 Hz, 1H) 7.63 (dd, J=8.22, 4.89 Hz, 1H) 7.99 (br. s., 1H). 19F NMR (377 MHz, CDCl3) δ ppm −90.65 (s, 1F). MS (ESI, pos. ion) m/z: 243.9/245.9 (M+1).
Workup
- customA 2 L 3-neck flask with a temperature probe adapter was fixed with a mechanical stirrer, condenser
- temperaturethe temperature raised to 100° C
- customThe heating mantle was replaced with an ice bath
- temperatureto cool the reaction mixture to RT
- additionthe brown solution was poured into a beaker
- additionadded to a separatory funnel
- extractionextracted with EtOAc (2×150 mL)
- dry with materialthe combined organics were dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-72742876e2204d05a8c871cc98406631
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394297B2
Linked notes
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