Phosphorus tribromide → 3-(4-(2-Bromoethyl)phenyl)-5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazole

HRID 1948554Notes

Reaction equation

[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][CH2:24]O)=[CH:19][CH:18]=4)[N:13]=3)[C:8]=2[CH2:26][CH2:27][CH3:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:30]>ClCCCl.ClCCl>[Br:30][CH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[N:13]=[C:12]([C:9]3[C:8]([CH2:26][CH2:27][CH3:28])=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[O:11][N:10]=3)[O:16][N:15]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 2-(4-(5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethanol (400 mg, 1.065 mmol) in DCE (20 mL) was added phosphorus tribromide in DCM (1.065 mL, 1.065 mmol). The reaction mixture was heated at 70° C. overnight. The reaction mixture was diluted with dichloromethane and washed with 1N NaOH. The organic layer was dried MgSO4, filtered, and concentrated. The crude material was purified on a 40 gram silica column and eluting with EtOAc/Hex (0-50% gradient over 20 minutes) to afford 77 mg of 3-(4-(2-bromoethyl)phenyl)-5-(5-phenyl-4-propylisoxazol-3-yl)-1,2,4-oxadiazole. MS (m+1)=440. HPLC Peak RT=2.40 minutes. (Analytical Method B).

Workup

washwashed with 1N NaOH
filtrationfiltered
concentrationconcentrated
customThe crude material was purified on a 40 gram silica column
washeluting with EtOAc/Hex (0-50% gradient over 20 minutes)

Sources & evidence

ORD record: ord-5cb5485ef1614d328e303af38965f5f5
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399451B2

Reaction notes

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