Triphenylphosphine → 3-(1-Bromo-ethyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazole

HRID 732044Notes

Reaction equation

HRID 732044 reaction equation
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:28][C:29]1[CH:30]=[C:31]([C:35]2[O:39][N:38]=[C:37]([CH:40](O)[CH3:41])[N:36]=2)[CH:32]=[CH:33][CH:34]=1>C1COCC1>[Br:1][CH:40]([C:37]1[N:36]=[C:35]([C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([Cl:28])[CH:30]=2)[O:39][N:38]=1)[CH3:41]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 578379411-[5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanol

Product 1

HCID 578379313-(1-Bromo-ethyl)-5-(3-chloro-phenyl)-[1,2,4]oxadiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 396 mg (2.22 mmol) N-bromosuccinimid in 2 ml THF was added dropwise to a solution of 583 mg (2.22 mmol) triphenylphosphine in 2 ml THF at 0° C. After stirring for 20 min 416 mg (1.85 mmol) 1-[5-(3-chloro-phenyl)-[1,2,4]oxadiazol-3-yl]-ethanol in 2 ml THF was added. Stirring was continued overnight at room temperature before the solvent was removed under reduced pressure. Flash chromatography (heptane/EtOAc 6:1) afforded 168 mg (32%). 1H NMR (CDCl3), d (ppm): 2.12 (d, 3 H) 5.21 (q, 1 H) 7.47 (t, 1 H) 7.57 (m, 1 H) 8.03 (d, 1 H) 8.15 (s, 1 H).

Workup

  1. additionwas added
  2. customwas removed under reduced pressure
  3. customFlash chromatography (heptane/EtOAc 6:1) afforded 168 mg (32%)

Sources & evidence

ORD record
ord-b27e38058aee4f36b56c92ff956a2da8
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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