Potassium Bromide → HCID 44194811, compound

HRID 1668431Notes

Reaction equation

HRID 1668431 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10](O)([CH3:18])[O:9][N:8]=2)=[CH:4][CH:3]=1.[K+].[Br-]>>[C:12]1([C:11]2[C:7]([C:5]3[O:6][C:2]([CH3:1])=[CH:3][CH:4]=3)=[N:8][O:9][C:10]=2[CH3:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 253877Potassium BromideHCID 67346689HCID 67346689, compound

Product 1

HCID 44194811HCID 44194811, compoundYield 60%

Procedure

Prepared with 60% yield by dehydration/aromatisation of 3-(5-methylfuran-2-yl)-4-phenyl-5-hydroxy-5-methyl-2-isoxazoline. 60% yield. Yellow oil. FT-IR (KBr): 3058, 2924, 2852, 1627, 1598, 1566, 1498, 1435, 1239, 1208, 1149, 1074, 1024, 922, 898, 791, 772, 701 cm−1. 1H NMR (400 MHz, CDCl3, δ): 7.44-7.40 (m, 3H, aromatic protons); 7.31-7.24 (m, 2H, aromatic protons); 6.12 (d, 1H, J=3.3 Hz, furyl protons); 5.94-5.92 (m, 1H, furyl protons); 2.36 (s, 3H); 2.32 (s, 3H). 13C NMR (100 MHz, CDCl3, δ): 166.3, 153.9, 153.0, 142.2, 130.1, 130.0, 128.6, 128.1, 112.8, 107.3, 13.6, 11.2. GC-MS (70 eV) m/z (int. rel.): 239 (M+, 48), 198 (15), 197 (100), 196 (23), 168 (5), 167 (6), 154 (7), 129 (7), 127 (5), 115 (5), 89 (4), 43 (7). 102 (10), 261 (100), 234 (10), 232 (10), 154 (54), 153 (33), 129 (12), 127 (31), 77 (9), 43 (14). Anal. Calc. for C15H13NO2: C, 75.30; H, 5.48; N, 5.85. Found: C, 75.08; H, 5.60; N, 5.90.

Sources & evidence

ORD record
ord-6b4f2945d867444d8b32b2ef6e925331
Source dataset
uspto-grants-2011_08
Patent number
US07989450B2

Reaction notes

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