Bromine → 1-Acetyl-5-bromo-2-methyl-4-(trifluoromethyl)-2,3-dihydro-1H-indole

HRID 2101927Notes

Reaction equation

HRID 2101927 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[CH3:17])(=[O:3])[CH3:2].[Br:18]Br.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([C:13]([F:16])([F:14])[F:15])[C:9]([Br:18])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[CH3:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 516892Sodium BicarbonateHCID 578001261-Acetyl-2-methyl-4-(trifluoromethyl)-2,3-dihydro-1H-indole

Product 1

HCID 578002541-Acetyl-5-bromo-2-methyl-4-(trifluoromethyl)-2,3-dihydro-1H-indoleYield 62.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-acetyl-2-methyl-4-(trifluoromethyl)-2,3-dihydro-1H-indole (0.100 g, 0.45 mmol; step A above) in acetic acid (1.0 mL) at rt was added bromine (0.035 mL; 0.68 mmol). More bromine (0.020 mL, 0.39 mmol) was added after 14 h. After another 5 h, the mixture was slowly added to sat'd NaHCO3 and extracted with Et2O (×3). Combined organics were washed (H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.090 g of the title compound as a white solid: MS (ES) m/z 324 (M+2 isomer).

Workup

  1. extractionextracted with Et2O (×3)
  2. washCombined organics were washed (H2O, brine)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-3b9ee4bd1c8745538cb66f8b8f07b433
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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