Triethylamine → 2-Bromo-1-(3-phenyl-2,3-dihydro-1H-indol-1-yl)propan-1-one

HRID 262296Notes

Reaction equation

HRID 262296 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].[C:7]1([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C1C=CC=CC=1>[Br:1][CH:2]([CH3:6])[C:3]([N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 979802-Bromopropanoyl chlorideHCID 109323533-phenyl-2,3-dihydro-1H-indole

Product 1

HCID 213204612-Bromo-1-(3-phenyl-2,3-dihydro-1H-indol-1-yl)propan-1-oneYield 96.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 3.0 g of 2-bromopropionylchloride in 5 ml of benzene was added dropwise at 10° C. to a mixture of 3.0 g of 3-phenylindoline, 3.0 ml of triethylamine in 30 ml of dry benzene. The mixture was then washed with water, the benzene layer dried over sodium sulfate and the solvent removed in vacuo at room temperature to leave 4.9 g of the desired N-(2-bromopropionyl)-3-phenylindoline as a resin.

Workup

  1. washThe mixture was then washed with water
  2. dry with materialthe benzene layer dried over sodium sulfate
  3. customthe solvent removed in vacuo at room temperature

Sources & evidence

ORD record
ord-4a59b7c62f2043449ee9658555c1c9b5
Source dataset
uspto-grants-1979_05
Patent number
US04153789

Reaction notes

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