Bromine → 5-Bromo-3,3-diethyl-1,3-dihydro-2H-indol-2-one

HRID 496682Notes

Reaction equation

HRID 496682 reaction equation
[CH2:1]([C:3]1([CH2:13][CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12])[CH3:2].C([O-])(=O)C.[Na+].[Br:20]Br>C(O)(=O)C.O>[Br:20][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:12])[C:3]2([CH2:1][CH3:2])[CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 151532213,3-diethyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 219862505-Bromo-3,3-diethyl-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 3,3-diethylindol-2-one (8 g, 40 mmol) and sodium acetate (4 g, 48 mmol) in acetic acid (100 ml) was treated with bromine (6.4 g, 40 mmol). After 30 min. the mixture was diluted with water and extracted with EtOAc (2×); the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, then brine, dried (MgSO4) and evaporated to afford the crude product (7.6 g, 75%). A sample was recrystallized from EtOAc/hexane to obtain 5-bromo-1,3-dihydro-3,3-diethyl-[2H]-indol-2-one, m. p. 164-165° C.; 1H-NMR (DMSO-d6) δ 10.45 (s, 1H), 7.41-7.40(d, 1H, J=2.2 Hz), 7.34-7.31 (m, 1H), 6.78-6.76 (d, 1H J=8.2 Hz), 1.78-1.65 (m, 4H), 0.50-0.46 (m, 6H); MS (−ESI) m/z 266/268 (M−H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washthe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution
  3. dry with materialbrine, dried (MgSO4)
  4. customevaporated
  5. customto afford the crude product (7.6 g, 75%)
  6. customA sample was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-8a83d6f5039a4d19af4225f050c3f71e
Source dataset
uspto-grants-2005_09
Patent number
US06946454B2

Reaction notes

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