Bromine → 936479-38-8

HRID 132603Notes

Reaction equation

HRID 132603 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13](=[O:15])[CH3:14])=[C:11]([CH3:16])[O:10][N:9]=2)=[CH:4][CH:3]=1.[Br:17]Br>C(Cl)(Cl)(Cl)Cl.CC(O)=O>[Br:17][CH2:14][C:13]([C:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[N:9][O:10][C:11]=1[CH3:16])=[O:15]

Participants

5

Reactant 2

HCID 24408BromineHCID 212961521-[3-(4-Bromophenyl)-5-methyl-4-isoxazolyl]ethanone

Product 1

HCID 87393006936479-38-8Yield 47%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a solution of 1-[3-(4-bromo-phenyl)-5-methyl-isoxazol-4-yl]-ethanone (2.49 g, 8.89 mmol) in carbontetrachloride (5.8 mL) and AcOH (0.3 mL) at 48° C. was added a solution of bromine (0.48 mL, 8.89 mmol) in carbontetrachloride (4.7 mL) over 10 min keeping the temperature below 50° C. After addition the reaction mixture was allowed to cool down to room temperature and poured into ice-water (20 mL). The layers were separated and the aqueous layer extracted with dichloromethane. The combined organic layers were then washed with water and brine, dried over Na2SO4 and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate:=8:2) afforded the title compound (1.49 g, 47%) as a light yellow oil. MS m/e: 355.9/358.1/360.0 [M+H]+.

Workup

  1. customthe temperature below 50° C
  2. additionAfter addition the reaction mixture
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with dichloromethane
  5. washThe combined organic layers were then washed with water and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customPurification by chromatography (SiO2, heptane:ethyl acetate:=8:2)

Sources & evidence

ORD record
ord-a68b9c7af9b0454480ce39e5fbc17d3c
Source dataset
uspto-grants-2008_06
Patent number
US07388025B2

Reaction notes

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