1,3-Dibromopropane → HCID 21910983, compound

Reaction equation

[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([OH:19])=[C:15]([CH2:16][CH2:17][CH3:18])[C:10]=3[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH2:22][CH2:23]Br.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:19][CH2:23][CH2:22][CH2:21][Br:20])=[C:15]([CH2:16][CH2:17][CH3:18])[C:10]=3[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Procedure

To a mixture of 3-phenyl-7-propyl-6-hydroxy-benz-[4,5]-isoxazole (1.0 g; 3.95 mmol, Prepared in Example 16 Step C), 1,3-dibromopropane (3.98g, 19.5 mmol) and potassium carbonate (0.573g, 4.15 mmol) in 4.0 mL of methyl ethyl ketone was warmed to reflux for 16 hours. Filtered, concentrated and chromatographed (silica gel, 30% ethyl acetate in hexane) to yeild 1.025 g of the title compound as a white solid. NMR (CDCl3): δ 7.95 (d,2H); 7.69 (d,1H); 7.55 (m,3H); 7.03 (d,1H); 4.25 (t,2H); 3.68 (t,2H); 2.95 (t,2H); 2.41 (m,2H); 1.76 (m,2H); 1.01 (t,3H)