3-Fluoroacetophenone → 3-Fluorophenacyl bromide

HRID 30153

Reaction equation

HRID 30153 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[Br:11]Br>O1CCOCC1>[Br:11][CH2:9][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)=[O:10]

Participants

4

Reactant 2

HCID 99673-FluoroacetophenoneHCID 24408Bromine

Product 1

HCID 27374513-Fluorophenacyl bromide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1-(3-fluorophenyl)ethanone (14.0 g, 100 mmol) (Aldrich) in dioxane (250 mL) at 12-15° C. was treated with a solution of bromine (17 g, 105 mmol) in dioxane (120 mL) drop wise over 0.5 h. This was stirred for 15 min and most of the solvent removed. The residue was taken up in hexane (200 mL), washed 2× water, and dried (MgSO4). Solvent was removed to give 2-bromo-1-(3-fluorophenyl)ethanone. 1H NMR (CDCl3), 300 MHz) δ3.71 (s, 2H, CH2), 7.30-7.77(m, 4H, Aromatic).

Workup

  1. customremoved
  2. washwashed 2× water
  3. dry with materialdried (MgSO4)
  4. customSolvent was removed

Sources & evidence

ORD record
ord-b5a4959aa8414c598e9a19d8cf9c0e80
Source dataset
uspto-grants-2008_09
Patent number
US07423053B2

Linked notes

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