Bromine → 131974-13-5

HRID 2219300Notes

Reaction equation

HRID 2219300 reaction equation
[C:1]1([C:7]2[C:11]([C:12](=[O:14])[CH3:13])=[CH:10][O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15]Br>C(Cl)(Cl)Cl.CC(O)=O>[Br:15][CH2:13][C:12]([C:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][O:9][CH:10]=1)=[O:14]

Participants

5

Reactant 2

HCID 24408BromineHCID 131964851-(3-Phenyl-1,2-oxazol-4-yl)ethan-1-one

Product 1

HCID 59949602131974-13-5Yield 41.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 1-(3-phenyl-isoxazoi-4-yl)-ethanone (6.35 g, 34 mmol) in chloroform (50 mL) and AcOH (1 mL) at 48° C. was added a solution of bromine (1.83 mL, 36 mmol) in chloroform (15 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 (200 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 sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate: 100:0 to 7:3) afforded the title compound (3.72 g, 41%) which was obtained as a light yellow solid. MS m/e (EI): 265.0/267.0 [M].

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 sodium sulphate
  7. customevaporated
  8. customPurification by chromatography (SiO2, heptane:ethyl acetate: 100:0 to 7:3)

Sources & evidence

ORD record
ord-d6b63fa91f614db390451c6a1786b685
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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