Hydrogen Bromide → 1-(2-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromo ethanone

HRID 1378596Notes

Reaction equation

HRID 1378596 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=1.[BrH:19].BrBr>C(O)(=O)C.ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:18])[CH:9]([C:10]1[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=1)[Br:19]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 24408Bromine2×HCID 542055631-(2-Fluorophenyl)-2-(4-methylthiophenyl)ethanone

Product 1

HCID 537994631-(2-Fluorophenyl)-2-(4-methylthiophenyl)-2-bromo ethanone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A 100 mL three necked round bottomed flask equipped with reflux condenser, magnetic stir bar, thermometer adapter, and constant pressure addition funnel was charged with 1-(2-fluorophenyl)-2-(4-methylthiophenyl)ethanone from Step 2, (4.36 g, 16.7 mmol), acetic acid (30 mL) and 33% HBr in acetic acid (0.5 mL). The solution was stirred and treated with bromine (17 mL, 16.8 mmol, 1.0M in acetic acid) from the addition funnel at such a rate that the bromine color was discharged rapidly, ca, 15 min. After an additional 50 minutes at room temperature, the solution was concentrated in vacuo to give a brown oil. The crude haloketone was dissolved in dichloromethane and washed with 1N NaHSO3, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 1-(2-fluorophenyl)-2-(4-methylthiophenyl)-2-bromo-ethanone as an oil that solidified upon standing (4.83 g, 85%): mp 58°-63° C. 1H NMR (CDCl3) 300 MHz 7.87 (td, J=7.6, 1.8Hz, 1H), 7.52 (m, 1H), 7.39 (d, J=8.3Hz, 2H), 7.27-7.03 (m, 4H), 6.34 (s, 1H), 2.45 (s, 3H). 19F NMR (CDCl3) -108.51 (m). Mass spectrum M+ =338.

Workup

  1. temperaturewith reflux
  2. additioncondenser, magnetic stir bar, thermometer adapter, and constant pressure addition funnel
  3. custom15 min
  4. concentrationthe solution was concentrated in vacuo
  5. customto give a brown oil
  6. washwashed with 1N NaHSO3
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-919c4757e44048aeb8458b6ad08a47f9
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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