Water → 4-[5-(4-n-Pentyloxyphenyl)isoxazol-3-yl]bromobenzene

HRID 1386625Notes

Reaction equation

HRID 1386625 reaction equation
[Cl-].[Br:2][C:3]1[CH:11]=[CH:10][C:6]([CH:7]=[N:8][OH:9])=[CH:5][CH:4]=1.[CH2:12]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=1)[CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.O>O1CCCC1>[CH2:12]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[O:9][N:8]=[C:7]([C:6]3[CH:10]=[CH:11][C:3]([Br:2])=[CH:4][CH:5]=3)[CH:25]=2)=[CH:20][CH:19]=1)[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27751191-Eth-1-ynyl-4-(pentyloxy)benzeneHCID 737528934-Bromobenzaldehyde oxime chloride

Product 1

HCID 211823474-[5-(4-n-Pentyloxyphenyl)isoxazol-3-yl]bromobenzeneYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 4-bromobenzaldehyde oxime chloride (647 mg) and 4-n-pentyloxy-phenylacetylene (650 mg) in tetrahydrofuran (7 ml) was added triethylamine (0.5 ml) in tetrahydrofuran (5 ml) dropwise at 40° C. The solution was stirred at 40° C. for 30 minutes, poured into water and extracted with ethyl acetate. The organic layer was washed with H2O, brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with acetonitrile. The precipitate was collected by filtration and dried to give 4-[5-(4-n-pentyloxyphenyl)isoxazol-3-yl]bromobenzene (0.59 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with H2O, brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvents were removed under reduced pressure
  5. customthe residue was triturated with acetonitrile
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-e92c0896ad6f4906a5ddc2f43ab28bad
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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