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

HRID 722399Notes

Reaction equation

HRID 722399 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 mixture is placed under nitrogen and cooled to −55° C. and then 800 ml of isopropenylmagnesium bromide at 0.5 M in THF are added dropwise. The mixture is left with stirring for 1 hour and then poured into saturated NH4Cl solution. It is extracted with ether, the extract is evaporated and then the residue is taken up in DCM. It is washed with saturated NaCl solution. It is dried and evaporated and then the residue is chromatographed on silica, eluting with an AcOEt/cyclohexane (1/9; v/v) mixture. This gives 10.7 g of the expected compound.

Workup

  1. waitThe mixture is left
  2. extractionIt is extracted with ether
  3. customthe extract is evaporated
  4. washIt is washed with saturated NaCl solution
  5. customIt is dried
  6. customevaporated
  7. customthe residue is chromatographed on silica
  8. washeluting with an AcOEt/cyclohexane (1/9; v/v) mixture

Sources & evidence

ORD record
ord-8995fdecd0bb4973b3c445375ef1fde8
Source dataset
uspto-grants-2006_11
Patent number
US07138424B2

Reaction notes

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