Acetic Acid → HCID 71743936, compound

HRID 2200166Notes

Reaction equation

HRID 2200166 reaction equation
[Br:1]Br.[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2([CH2:14][CH2:13]2)[C:5]1=[O:15].C([O-])(=O)C.[Na+].C(O)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Br:1][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[N:4]([CH3:3])[C:5](=[O:15])[C:6]12[CH2:14][CH2:13]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 517045Sodium AcetateHCID 14317864HCID 14317864, compound

Product 1

HCID 71743936HCID 71743936, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add bromine (1.4 g, 8.7 mmol) dropwise to the mixture of 1′-methylspiro[cyclopropane-1,3′-indolin]-2′-one (1.5 g, 8.7 mmol), sodium acetate (0.7 g, 8.7 mmol) and acetic acid (0.52 g, 8.7 mmol) in dichloromethane (15 mL) at 0° C. After addition, stir the resulting mixture at room temperature overnight. Pour the reaction mixture to the cold sodium thiosulfate solution, extract with ethyl acetate (100 mL×2), combine the organic layers, and wash with brine (20 mL), dry over anhydrous sodium sulfate. Concentrate the solution under reduced pressure to give the crude product, purify by flash chromatography (silica gel, EtOAc:PE=1:5) to afford the title compound (1.0 g, 47.6%). MS: (M+1): 254.

Workup

  1. additionAfter addition
  2. extractionextract with ethyl acetate (100 mL×2)
  3. washwash with brine (20 mL)
  4. dry with materialdry over anhydrous sodium sulfate
  5. concentrationConcentrate the solution under reduced pressure
  6. customto give the crude product
  7. custompurify by flash chromatography (silica gel, EtOAc:PE=1:5)

Sources & evidence

ORD record
ord-ebd655cf4793463e8a2154c72a89e463
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

Loading…