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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1724029Generated: November 1, 2026

Benzyl Bromide → 1-benzyl-2-methyl-2,3-dihydro-1H-indole

https://huagongshe.com/reaction/1724029

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzyl BromideHCID 7498—
ReactantPotassium CarbonateHCID 11430—
Reactant2-MethylindolineHCID 23305—
ReactantAmmonium ChlorideHCID 25517—
SolventDiethyl EtherHCID 3283—
SolventDimethylformamideHCID 6228—
Product1-benzyl-2-methyl-2,3-dihydro-1H-indoleHCID 10513589101.5%

Reaction Steps

To a solution of 1 g (7.5 mmol) of 2-methyl-2,3-dihydro-1H-indole in anhydrous DMF were added 1.03 g (7.5 mmol) of K2CO3 and then dropwise 0.97 mL (8.0 mmol) of benzylbromide. The mixture was stirred at RT for 3 hrs and then distributed between Et2O and a saturated aqueous solution of NH4Cl. The combined organic phases were dried over Na2SO4 and evaporated to yield 1.7 g (quantitative) of crude 1-benzyl-2-methyl-2,3-dihydro-1H-indole, light blue oil, MS: 224 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07485652B2
Source datasetuspto-grants-2009_02
ORD IDord-7bf7653bb0f34916bd2c847cb2d88868
Source noteuspto-grants-2009_02