Acetic Acid → 5-Bromo-7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one

HRID 2250518Notes

Reaction equation

HRID 2250518 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2([CH3:13])[CH3:12].C(O)(=O)C.[Br:18]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Br:18][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([F:1])[CH:3]=1)[NH:9][C:8](=[O:11])[C:7]2([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 119764367-fluoro-3,3-dimethyloxindole

Product 1

HCID 119764375-Bromo-7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-oneYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (4.1 g, 22.9 mmol) was dissolved in dichloromethane (100 mL) and acetic acid (2 mL) at room temperature. Bromine (1.2 mL, 23 mmol) was added and the solution allowed to stir for 24 hours. The reaction mixture was poured into sodium thiosulfate solution, extracted with diethyl ether, dried (MgSO4), evaporated and the crude product triturated with hexane to give 5-bromo-7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (4.84 g, 82%): HRMS: calc'd for C10H9BrFNO, 256.9852; found (ESI, [M−H]−), 255.9781.

Workup

  1. customat room temperature
  2. extractionextracted with diethyl ether
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customthe crude product triturated with hexane

Sources & evidence

ORD record
ord-2de8ad64d7844f0b9071c0b2204d01d2
Source dataset
uspto-grants-2008_01
Patent number
US07317037B2

Reaction notes

Loading…