Acetic Acid → HCID 24824338, compound

HRID 2250522Notes

Reaction equation

HRID 2250522 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:13])([CH3:12])[C:5](=[O:11])[NH:6]2.C(O)(=O)C.[Br:18]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Br:18][C:10]1[C:2]([F:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5](=[O:11])[C:4]2([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 248243364-Fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 24824338HCID 24824338, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (1 g, 22.9 mmol) was dissolved in dichloromethane (DCM) (50 mL) and acetic acid (2 mL) at room temperature. Bromine (0.386 mL, 7.5 mmol) was added and the solution allowed to stir 24 hours. The reaction mixture was poured into sodium thiosulfate solution, extracted with diethyl ether, the combined organic layers were dried over magnesium sulfate and evaporated. Trituration of the crude product with hexane gave 5-bromo-4-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (1.25 g, 87%): HRMS [M−H]− 255.9781

Workup

  1. customat room temperature
  2. extractionextracted with diethyl ether
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-8ade7d237a0345abaab32bf7cb50bfc6
Source dataset
uspto-grants-2008_01
Patent number
US07317037B2

Reaction notes

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