1-Bromo-2-nitrobenzene → 7-Bromoindole

HRID 2199734Notes

Reaction equation

HRID 2199734 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[CH:11]([Mg]Br)=[CH2:12].[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 113411-Bromo-2-nitrobenzeneHCID 25517Ammonium ChlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 27570207-Bromoindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

1-bromo-2-nitrobenzene (6.000 g, 29.7 mmol) was added to tetrahydrofuran (65 mL) and cooled to −40° C. Vinylmagnesiumbromide (1M in tetrahydrofuran, 89 mL) was added quickly. The solution was stirred for 20 minutes and then poured into a saturated aqueous solution of ammonium chloride. The solution was extracted with diethyl ether and dried with brine and anhydrous sodium sulfate. The solution was concentrated and purified by flash column chromatography on silica gel with 5% ethyl acetate in hexanes to provide the title compound.

Workup

  1. extractionThe solution was extracted with diethyl ether
  2. dry with materialdried with brine and anhydrous sodium sulfate
  3. concentrationThe solution was concentrated
  4. custompurified by flash column chromatography on silica gel with 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0d3ea9c378374513a072d8c7506debd8
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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