Bromine → HCID 86723945, compound

HRID 1475325Notes

Reaction equation

HRID 1475325 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][C:5]2([CH3:12])[CH3:11].[Br:13]Br>OS(O)(=O)=O.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[Br:13][N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[C:5]([CH3:12])([CH3:11])[CH2:6]1

Participants

5

Reactant 2

HCID 24408BromineHCID 217125755-Fluoro-3,3-dimethylindoline

Product 1

HCID 86723945HCID 86723945, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 159865Silver sulfateCatalystHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 5-fluoro-3,3-dimethyl-2,3-dihydro-1H-indole (1.6 g, 9.6 mmol) in 98% H2SO4 (20 mL), Ag2SO4 (1.6 g, 5.1 mmol) was added and the suspension was stirred under nitrogen for 30 minutes. The mixture was then cooled to −5° C., Br2 (508 μL, 9.9 mmol) was slowly added over 15 minutes and stirring maintained at the same temperature for 1 h. The reaction mixture was slowly poured over 200 mL of water/ice and subsequently filtered through Celite. 50% aqueous NaOH was added to the resulting solution (to pH ═9-10) and the product was extracted with EtOAc (3×). The organic phase was dried (MgSO4), filtered and concentrated to give the title compound (1.58 g) as a dark oil. 1H NMR (DMSO-d6): 7.03 (1H, d), 6.64 (1H, d), 5.59 (1H, s), 3.20 (2H, s), 1.25-1.15 (6H, m). MS: [M+H]+=244.

Workup

  1. stirringstirring
  2. temperaturemaintained at the same temperature for 1 h
  3. filtrationsubsequently filtered through Celite
  4. addition50% aqueous NaOH was added to the resulting solution (to pH ═9-10)
  5. extractionthe product was extracted with EtOAc (3×)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5955d9794f034bf9ae2a80903e7dc722
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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