Bromine → 2-Bromo-1-(3-ethyl-4-fluoro-phenyl)-ethanone

HRID 2415259Notes

Reaction equation

HRID 2415259 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][C:8]=1[F:9])[CH3:2].[Br:13]Br>O1CCOCC1>[Br:13][CH2:11][C:10]([C:5]1[CH:6]=[CH:7][C:8]([F:9])=[C:3]([CH2:1][CH3:2])[CH:4]=1)=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 22641004Ethanone, 1-(3-ethyl-4-fluorophenyl)-

Product 1

HCID 226409982-Bromo-1-(3-ethyl-4-fluoro-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1-(3-ethyl-4-fluoro-phenyl)-ethanone (400 mg, 2.41 mmol) (from Step D) in 1,4-dioxane, bromine (124 μL, 2.41 mmol) was added and the mixture was stirred for 30 minute. at room temperature. The solvent was removed and the residue was chromatographed (5% dichloromethane/hexanes) to give an oil. 317 mg, 54%. 1H NMR(CDCl3, 300 MHz), σ 1.2-1.35 (t, 3H), 2.67-2.80 (q, 2H), 4.42 (s, 2H), 7.03-7.0 (t, 1H), 4.45 (s, 2H), 7.75-7.92 (m, 2H).

Workup

  1. customat room temperature
  2. customThe solvent was removed
  3. customthe residue was chromatographed (5% dichloromethane/hexanes)
  4. customto give an oil

Sources & evidence

ORD record
ord-9c45b4cf8f20407094282b4f98de716c
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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