Triethylamine → Ethyl 3-(4-bromo-2-fluorophenyl)-5-methylisoxazole-4-carboxylate

HRID 434049Notes

Reaction equation

HRID 434049 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:3]=1[C:4](=[N:6][OH:7])Cl.[CH2:13]([O:15][C:16](=[O:20])[C:17]#[C:18][CH3:19])[CH3:14].C(N(CC)CC)C>C(OCC)C>[CH2:13]([O:15][C:16]([C:17]1[C:4]([C:3]2[CH:8]=[CH:9][C:10]([Br:12])=[CH:11][C:2]=2[F:1])=[N:6][O:7][C:18]=1[CH3:19])=[O:20])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78043Ethyl 2-butynoateHCID 734619254-Bromo-2-fluoro-N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 18756263Ethyl 3-(4-bromo-2-fluorophenyl)-5-methylisoxazole-4-carboxylateYield 83.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a fashion similar to that described for preparation 15, 2-fluoro-4-bromo-benzoyl chloride oxime (2.00 g, 7.92 mmol), ethyl-2-butynoate (1.33 g, 11.9 mmol), triethylamine (2.2 ml, 15.8 mmol) in diethyl ether (10 ml), and diethyl ether (20 ml) gave 4-ethoxycarbonyl-5-methyl-3-(2-fluoro-4-bromophenyl)isoxazole (2.16 g, 83%) after column chromatography (silica gel, hexanes/diethyl ether gradient). 1H NMR (400 MHz, CDCl3) δ 7.36-7.29 (m, 3H), 4.16 (q, 2H, J=6.8 Hz), 2.70 (s, 3H), 1.15 (t, 3H, J=6.9 Hz)ppm.

Sources & evidence

ORD record
ord-1ab1d7ed4034442fab68573138d9cf5a
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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