Water → 5-bromo-1-(phenylacetyl)-2,3-dihydro-1H-indole

HRID 1510224Notes

Reaction equation

HRID 1510224 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.C(N(CC)CC)C.[C:18]1([CH2:24][C:25](Cl)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:25](=[O:26])[CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 34115665-Bromoindoline

Product 1

HCID 668241055-bromo-1-(phenylacetyl)-2,3-dihydro-1H-indoleYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromoindoline (13.86 g) and triethylamine (8.50 g) in dichloromethane (100 mL) was added dropwise phenylacetyl chloride (11.9 g) at 5° C. and the mixture was stirred at ambient temperature for 16 hours. The mixture was poured into water and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to give 5-bromo-1-(phenylacetyl)indoline (16.01 g) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-3c7bd4253d1e43b39784440f2bec726b
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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