1-Bromo-2-nitrobenzene → 7-Bromo-2-methylindole

HRID 890237Notes

Reaction equation

HRID 890237 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([Mg]Br)([CH3:13])=[CH2:12].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][C:11]([CH3:13])=[CH:12]2

Participants

5

Reactant 3

HCID 113411-Bromo-2-nitrobenzeneHCID 25517Ammonium ChlorideHCID 178456138HCID 178456138, compound

Product 1

HCID 44130817-Bromo-2-methylindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-55 °C

Procedure

27.0 g of 2-bromonitrobenzene are placed in 400 ml of THF. The medium is placed under nitrogen and is cooled to −55° C. and then 800 ml of 0.5M isopropenylmagnesium bromide in THF are added dropwise. The medium is left stirring for 1 hour and then it is poured into a saturated NH4Cl solution. Extraction is carried out with ether, the extract is evaporated and then the residue is taken up in DCM. Washing is carried out with a saturated NaCl solution. The organic layer is dried and evaporated and then the residue is chromatographed on silica while eluting with an AcOEt/cyclohexane (1/9, v/v) mixture. 10.7 g of the expected compound are obtained.

Workup

  1. waitThe medium is left
  2. extractionExtraction
  3. customthe extract is evaporated
  4. washWashing
  5. customThe organic layer is dried
  6. customevaporated
  7. customthe residue is chromatographed on silica
  8. washwhile eluting with an AcOEt/cyclohexane (1/9, v/v) mixture

Sources & evidence

ORD record
ord-46f31e3bf53946d9b4fc969d470627b5
Source dataset
uspto-grants-2006_02
Patent number
US06995184B2

Reaction notes

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