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Bromine → 5-Bromo-7-fluoro-1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

HRID 2250527
Notes
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Reaction equation

HRID 2250527 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8](=[O:12])[C:7]2([CH3:14])[CH3:13].C([O-])(=O)C.[Na+].[Br:20]Br>C(Cl)Cl>[Br:20][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([F:1])[CH:3]=1)[N:9]([CH3:11])[C:8](=[O:12])[C:7]2([CH3:14])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 57439917HCID 57439917, compound

Product 1

HCID 574399185-Bromo-7-fluoro-1,3,3-trimethyl-1,3-dihydro-2H-indol-2-oneYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

7-Fluoro-1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one (0.10 g, 0.52 mmol) was dissolved in 5 mL of CH2Cl2 and sodium acetate (47 mg, 0.56 mmol) was added followed by bromine (0.029 mL, 0.56 mmol). The mixture was stirred at 25° C. for 16 h then loaded directly onto a silica gel column. The column was eluted with 250 mL of CH2Cl2 and 250 mL 5% Acetone/CH2Cl2 to provide the title compound (116 mg) as a white solid (82%).

Workup

  1. washThe column was eluted with 250 mL of CH2Cl2 and 250 mL 5% Acetone/CH2Cl2

Sources & evidence

ORD record
ord-8df9bd0ec6af41e5b2b6cf6b42eba172
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07317037B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes