Water → HCID 44194810, compound

HRID 1668433Notes

Reaction equation

HRID 1668433 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]([CH3:17])[O:8][N:7]=1.C1C(=O)N([Br:25])C(=O)C1.O.[K+].[Br-]>CN(C=O)C.CCCCCC.C(OCC)(=O)C>[Br:25][C:5]1[O:1][C:2]([C:6]2[C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[C:9]([CH3:17])[O:8][N:7]=2)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 253877Potassium BromideHCID 57780771HCID 57780771, compound

Product 1

HCID 44194810HCID 44194810, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(furan-2-yl)-4-phenyl-5-methylisoxazole (0.152 g, 0.670 mmol) in anhydrous DMF (6 ml), kept stirring at 0° C., is slowly added NBS (0.144 g, 0.810 mmol). A suspension is formed which is kept stirring for 2 h at ambient temperature. Water is then added, and then ethyl acetate. The two phases are separated and the aqueous phase is extracted three times with ethyl acetate. The total organic phase is first washed with a saline aqueous solution (NaCl) and then dried with anhydrous Na2SO4. The solvent is evaporated at reduced pressure. A yellow solid is obtained. When subjected to chromatography (silica gel, petroleum ether/ethyl acetate=9:1) it gave the product with 60% yield, as a white solid; m.p. 93-96° C. (hexane). FT-IR (KBr): 3143, 3055, 2962, 2923, 2851, 1632, 1605, 1505, 1434, 1408, 1236, 1202, 1122, 1019, 984, 921, 896, 796, 774, 721, 704, 676, 561 cm−1. 1H NMR (400 MHz, CDCl3, δ): 7.44-7.35 (m, 3H, aromatic protons); 7.26-7.23 (m, 2H, aromatic protons); 6.24 (d, 1H, J=3.3 Hz, furyl proton); 6.20 (d, 1H, J=3.3 Hz, furyl proton); 2.34 (s, 3H). 13C NMR (100 MHz, CDCl3, δ): 166.7, 152.1, 145.8, 129.9, 129.3, 128.7, 128.3, 124.1, 114.6, 113.8, 112.9, 11.1. GC-MS (70 eV) m/z (rel.int.): 305 [(M++2), 47], 303 (M+, 100), 264 (13), 263 (98), 262 (23), 261 (100), 234 (10), 232 (10), 154 (54), 153 (33), 129 (12), 127 (31), 77 (9), 43 (14). Anal. Calc. For C14H10BrNO2: C, 55.29; H, 3.31; N, 4.61. Found: C, 55.08; H, 3.60; N, 4.20.

Workup

  1. customA suspension is formed which
  2. customThe two phases are separated
  3. extractionthe aqueous phase is extracted three times with ethyl acetate
  4. washThe total organic phase is first washed with a saline aqueous solution (NaCl)
  5. dry with materialdried with anhydrous Na2SO4
  6. customThe solvent is evaporated at reduced pressure
  7. customA yellow solid is obtained
  8. customgave the product with 60% yield

Sources & evidence

ORD record
ord-154311c04c934cf8af8c8c8ae320420c
Source dataset
uspto-grants-2011_08
Patent number
US07989450B2

Reaction notes

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