Diethylamine → N-ethyl-N-(2-fluoro-4-iodobenzyl)ethanamine

HRID 56078Notes

Reaction equation

HRID 56078 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:4]=1[F:10].[CH2:11]([NH:13][CH2:14][CH3:15])[CH3:12]>CCO>[CH2:11]([N:13]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:4]=1[F:10])[CH2:14][CH3:15])[CH3:12]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 222404061-(Bromomethyl)-2-fluoro-4-iodobenzene

Product 1

HCID 90022808N-ethyl-N-(2-fluoro-4-iodobenzyl)ethanamineYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(bromomethyl)-2-fluoro-4-iodobenzene (1.89 g, 6.0 mmol) and a solution of diethylamine (2.19 g, 30 mmol) in EtOH (60 mL) was stirred at rt overnight under N2, then concentrated in vacuo. The residue was dissolved in EtOAc (100 mL), and washed with water (100 mL×3) followed by brine (100 mL). The organic phase was concentrated in vacuo to give the title compound as colorless oil (1.72 g, 94%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (100 mL)
  3. washwashed with water (100 mL×3)
  4. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-09eac039fcb240d299595f50e5735ec9
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

Loading…