2,6-Lutidine → (4-Bromo-3,5-dimethyl-phenyl)-(2-fluoro-ethyl)-amine

HRID 1755017Notes

Reaction equation

HRID 1755017 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH2:9])=[CH:4][C:3]=1[CH3:10].[F:11][CH2:12][CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O.N1C(C)=CC=CC=1C>CC(N(C)C)=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:9][CH2:13][CH2:12][F:11])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 123831174-Bromo-3,5-dimethylaniline

Product 1

HCID 86672778(4-Bromo-3,5-dimethyl-phenyl)-(2-fluoro-ethyl)-amineYield 53.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 4-bromo-3,5-dimethyl-phenylamine (400 mg, 2 mmol), toluene-4-sulfonic acid 2-fluoro-ethyl ester (567 mg, 2.6 mmol) and 2,6-lutidine (429 mg, 4.0 mmol) in DMA (5 ml) was heated with stirring at 120° C. for four hours. The mixture was quenched with water and then extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to give (4-bromo-3,5-dimethyl-phenyl)-(2-fluoro-ethyl)-amine (262 mg, 53%).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was sequentially washed with water and saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-12090771721c415793caeb9ec6be4048
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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