Bromine → 2-Bromo-4'-(methylsulfonyl)acetophenone

HRID 1743893Notes

Reaction equation

HRID 1743893 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].[Br:14]Br>C(O)(=O)C.Cl.O>[Br:14][CH2:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:8][CH:9]=1)=[O:3]

Participants

6

Reactant 2

HCID 24408BromineHCID 825294-Methylsulfonylacetophenone

Product 1

HCID 7358232-Bromo-4'-(methylsulfonyl)acetophenoneYield 109.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of the acetophenone prepared in Step 2 (11.91 g, 60.5 mmol) in glacial acetic acid (133 ml) and hydrochloric acid (0.11 ml) at ambient temperature, was added a solution of bromine (8.22 g, 51.4 mmol) in glacial acetic acid (9.3 ml) over a period of three hours. The reaction mixture was diluted with water (500 ml) and extracted with chloroform. The combined chloroform extracts were dried (MgSO4) and concentrated in vacuo to give 15.66 g of crude 2-bromo-4′-(methylsulfonyl)acetophenone: 1H NMR (CDCl3) δ3.10 (s, 3H), 4.45 (s, 2H), 8.08 (d, J=9 Hz, 2H), 8.17 (d, J=9 Hz, 2H). The sample was used without further purification.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe combined chloroform extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2390aadac72c41fabfe9b1fda20bd66f
Source dataset
uspto-grants-2006_03
Patent number
US07012094B1

Reaction notes

Loading…