Sodium Hydroxide → 4-Bromo-6-fluoro-1H-indole

HRID 2421240Notes

Reaction equation

HRID 2421240 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+]([O-])=O)[C:3]=1/[CH:12]=[CH:13]/[N:14](C)C.[OH-].[Na+]>C(O)(=O)C.O.[Zn]>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]2[C:3]=1[CH:12]=[CH:13][NH:14]2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59627932HCID 59627932, compound

Product 1

HCID 247281734-Bromo-6-fluoro-1H-indoleYield 12.9%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of crude[(E)-2-(2-bromo-4-fluoro-6-nitrophenyl)ethenyl]dimethylamine (D15) (6.07 g, 21.0 mmol) in acetic acid (200 mL) and water (50.0 mL) at 75° C. was added zinc powder (15.11 g, 231 mmol) portionwise over 1 hour. The mixture was heated to 85° C. and stirred for 4 hours. After cooling to room temperature, the reaction mixture was neutralised by the addition of 50% aqueous sodium hydroxide solution. The product was extracted into diethyl ether. After separation of the layers, the aqueous phase was re-extracted with diethyl ether. The combined organic layers were dried over magnesium sulphate, filtered and concentrated. The product was partially purified by silica gel chromatography eluting with 5-30% ethyl acetate in hexane. Purer fractions were combined to give the title compound (D16), (580 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe product was extracted into diethyl ether
  3. customAfter separation of the layers
  4. extractionthe aqueous phase was re-extracted with diethyl ether
  5. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was partially purified by silica gel chromatography
  9. washeluting with 5-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-fe9db969507d4328a8c43078391c2cd1
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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