Benzyl Bromide → 1-benzylindoline

HRID 225779Notes

Reaction equation

HRID 225779 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO>[CH2:16]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10328IndolineHCID 11430Potassium Carbonate

Product 1

HCID 108050961-benzylindolineYield 83.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Indoline (12.70 g, 106.5 mmol) was dissolved in MeOH (120 ml), stirred at room temperature and treated with potassium carbonate (14.70 g, 106.5 mmol). Benzyl bromide (18.20 g, 106.5 mmol) was then added and the mixture heated to reflux for 4 hr. The solution was cooled and filtered to remove the carbonate. The filtered solution was washed with water (2×100 ml) and extracted into DCM (2×100 ml), dried (MgSO4) and reduced under vacuum to give the title compound (18.65 g, 83%) as a brown semisolid. δH (d6 DMSO) 7.27 (5H, br m), 6.98 (1H, t), 6.95 (1H, t), 6.50 (2H, d), 4.18 (2H, s), 3.17 (2H, t, J 7.3 Hz), 2.84 (2H, t, J 7.2 Hz); m/z (ES+, 70V) 210 (MH+).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 hr
  3. temperatureThe solution was cooled
  4. filtrationfiltered
  5. customto remove the carbonate
  6. washThe filtered solution was washed with water (2×100 ml)
  7. extractionextracted into DCM (2×100 ml)
  8. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-c05546b892a4422e96ed5912a2262a56
Source dataset
uspto-grants-2009_07
Patent number
US07557130B2

Reaction notes

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