Hydrogen Bromide → HCID 54373829, compound

HRID 1378579Notes

Reaction equation

HRID 1378579 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:18])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[BrH:19].BrBr>C(O)(=O)C>[Br:19][CH:10]([C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)[C:9]([C:6]1[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=1)=[O:18]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 114709614-Fluorophenyl-1-[4-(methylthio)phenyl]ethanone

Product 1

HCID 54373829HCID 54373829, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred slurry of 2-(4-fluorophenyl)-1-(4-methylthiophenyl)ethanone from Step 1 (5.04 g, 19.36 mmol) in acetic acid (100 mL) was added HBr in acetic acid (45 mL, 48% by wt.) and bromine (1.0 mL, 3.09 g, 19.36 mmol). The resulting green slurry became homogeneous within 30 minutes. After 4 hours, the reaction was concentrated in vacuo, the residue diluted with toluene, and reconcentrated in vacuo. The crude haloketone was purified by flash chromatography (2:1 hexane:methylene chloride) and recrystallized from ethyl acetate and isooctane yielding 2-bromo-2-(4-fluorophenyl)-1-(4-methylthiophenyl)ethanone as an off-white solid (4.51 g, 69%): mp 108°-111° C. 1H NMR (CDCl3) 300 mHz δ7.94 (d, J=8.79 Hz, 2H), 7.60-7.50 (m, 2H), 7.25 (d, J=8.79 Hz, 2H), 7.10 (t, J=8.67 Hz, 2H), 6.34 (s, 1H), 2.56 (s, 3 H).

Workup

  1. waitAfter 4 hours
  2. concentrationthe reaction was concentrated in vacuo
  3. additionthe residue diluted with toluene
  4. customThe crude haloketone was purified by flash chromatography (2:1 hexane:methylene chloride)
  5. customrecrystallized from ethyl acetate and isooctane

Sources & evidence

ORD record
ord-d5f610a5427c48518df9be42e3a6c739
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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