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

HRID 650550Notes

Reaction equation

HRID 650550 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)acetophenone

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 a of crude 2-bromo-4′-(methylsulfonyl) acetophenone:

Workup

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

Sources & evidence

ORD record
ord-57207c5cf8c3455c805b62acb48b8d5f
Source dataset
uspto-grants-2001_08
Patent number
US06274590B1

Reaction notes

Loading…