Bromine → HCID 86724010, compound

HRID 1475414Notes

Reaction equation

HRID 1475414 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[NH:4][CH2:3]1.[Br:13]Br>S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:13][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:12])([CH3:1])[CH2:3][NH:4]2)=[CH:9][C:8]=1[CH3:11]

Participants

5

Reactant 2

HCID 24408BromineHCID 153993532,3-Dihydro-3,3,5-trimethyl-1H-indole

Product 1

HCID 86724010HCID 86724010, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 1118Sulfuric AcidSolvent

Procedure

3,3,5-Trimethyl-2,3-dihydro-1H-indole (1.84 g, 11.43 mmol) was dissolved in concentrated sulfuric acid (25 mL) and silver sulfate (1.90 g, 6.06 mmol) added. The reaction was stirred for 1 h and bromine (0.6 mL, 11.77 mmol) was added over 5 minutes. The reaction was stirred at this temperature for 1 h and very slowly quenched by slow addition to 50% aqueous sodium hydroxide (100 mL) with ice cooling (CAUTION,). Further aqueous sodium hydroxide was added to adjust pH to basic. The resulting mixture was extracted with diethyl ether (3×) and the organic phase dried over sodium sulfate, filtered and concentrated. Chromatography (silica gel, gradient elution, 0-50%, EtOAc in petrol 40-60), to give the title compound (1.30 g), MS: [M+H]+=241.

Workup

  1. stirringThe reaction was stirred at this temperature for 1 h
  2. customvery slowly quenched by slow addition to 50% aqueous sodium hydroxide (100 mL) with ice cooling (CAUTION,)
  3. additionFurther aqueous sodium hydroxide was added
  4. extractionThe resulting mixture was extracted with diethyl ether (3×)
  5. dry with materialthe organic phase dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washChromatography (silica gel, gradient elution, 0-50%, EtOAc in petrol 40-60)

Sources & evidence

ORD record
ord-07664c9bfaf049208c46c9c61c74e8e6
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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