Hydrogen Bromide → 2-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

HRID 1378584Notes

Reaction equation

HRID 1378584 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[BrH:21].BrBr>C(O)(=O)C>[Br:21][CH:9]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=1)[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:20]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 112433011-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone

Product 1

HCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanoneYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred slurry of 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl) ethanone from Step 1 (3.03 g, 10.38 mmol) in acetic acid (40 mL) was added HBr in acetic acid (2 mL, 48% by wt. ) and bromine (0.64 mL, 1.99 g, 12.45 mmol). Within minutes the slurry became homogeneous. After 1 hour, the reaction was concentrated in vacuo, diluted with methylene chloride and reconcentrated in vacuo yielding 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl) ethanone as a tan solid (3.53 g, 95%) which could be used without further purification. mp 140°-141° C., 1H NMR (CDCl3) 300 mHz δ8.05 (dd, J=5.16, 8.84 Hz, 2H), 7.96 (d, J=8.48 Hz, 2H), 7.75 (d, J=8.48 Hz, 2H), 7.17 (t, J=8.48 Hz, 2H), 6.29 (s, 1H), 3.06 (s, 3H). MS: m/e 371/373 (MH+). HRMS Δ=5.5 mmu.

Workup

  1. waitWithin minutes the slurry became homogeneous
  2. concentrationthe reaction was concentrated in vacuo
  3. additiondiluted with methylene chloride

Sources & evidence

ORD record
ord-75f85d8bbbb74d44b95529581756d08e
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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