Diethyl Ether → 4-Bromo-3-(2,3-dihydro-indol-1-ylmethyl)-benzonitrile

HRID 1859205Notes

Reaction equation

HRID 1859205 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10]Br.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1.C(N(CC)CC)C.CCOCC>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 10328IndolineHCID 114713444-Bromo-3-(bromomethyl)benzonitrile

Product 1

HCID 221232864-Bromo-3-(2,3-dihydro-indol-1-ylmethyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-bromo-3-bromomethyl-benzonitrile (2.66 g, 9.7 mmol), indoline (1.14 mL, 10.2 mmol) and triethylamine (1.60 mL, 11.5 mmol) was heated at reflux for 18 h in dry tetrahydrofuran (50 mL). The flask was cooled and ether (100 mL) was added. Evaporation gave crude 4-bromo-3-(2,3-dihydro-indol-1-ylmethyl)-benzonitrile.

Workup

  1. temperaturewas heated
  2. temperatureThe flask was cooled
  3. customEvaporation

Sources & evidence

ORD record
ord-ffc3e5abe42642188546013b39817110
Source dataset
uspto-grants-2000_11
Patent number
US06153641

Reaction notes

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