Potassium Bromide → 3-(5-Chloro-2-furanyl)-4-(4-fluorophenyl)-5-methylisoxazole

HRID 1668430Notes

Reaction equation

HRID 1668430 reaction equation
[Cl:1][C:2]1[O:6][C:5]([C:7]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:10](O)([CH3:19])[O:9][N:8]=2)=[CH:4][CH:3]=1.[K+].[Br-]>>[Cl:1][C:2]1[O:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:10]([CH3:19])[O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 253877Potassium BromideHCID 57780778HCID 57780778, compound

Product 1

HCID 441948133-(5-Chloro-2-furanyl)-4-(4-fluorophenyl)-5-methylisoxazoleYield 89%

Procedure

Prepared by dehydration/aromatisation of 3-(5-chlorofuran-2-yl)-4-(4-fluorophenyl)-5-hydroxy-5-methyl-2-isoxazoline. 89% yield. M.p. 103.7-105.2° C. FT-IR (KBr): 3147, 3077, 2931, 1637, 1595, 1522, 1508, 1445, 1418, 1403, 1236, 1230, 1223, 1203, 1158, 1135, 1018, 987, 939, 921, 896, 846, 794 cm−1. 1H NMR (500 MHz, CDCl3, δ): 7.28-7.26 (m, 2H, aromatic protons); 7.16-7.13 (m, 2H, aromatic protons); 6.29 (d, J=3.5 Hz, 1H, furyl proton); 6.15 (d, J=3.5 Hz, 1H, furyl proton); 2.37 (s, 3H, CH3). 13C NMR (75 MHz, CDCl3, δ): 167.0, 163.6, 161.7, 152.2, 143.4, 138.5, 131.8, 131.7, 125.3, 125.3, 116.0, 115.8, 113.8, 113.5, 107.9, 11.2. GC-MS (70 eV) m/z (rel.int.): 279 (M++2, 16), 277 (M+, 49), 237 (35), 236 (19), 235 (100), 234 (12), 206 (12), 172 (46), 171 (20), 170 (11), 147 (16), 145 (20), 89 (13), 43 (30). Anal. Calc. for C14H9ClFNO2: C, 60.56; H, 3.27; N, 5.04. Found: C, 60.58; H, 3.24; N, 5.01.

Sources & evidence

ORD record
ord-5e0a277b89fe43b0862a42ea6a4fda14
Source dataset
uspto-grants-2011_08
Patent number
US07989450B2

Reaction notes

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