Benzoyl chloride → [5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-phenyl-methanone

HRID 572299Notes

Reaction equation

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

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 57606117HCID 57606117, compound

Product 1

HCID 25211604[5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-phenyl-methanoneYield 70%

Procedure

Prepared from 4-Methyl-3-thiophen-2-yl-5-trifluoromethyl-isoxazole and benzoyl chloride by the method described in Example 3. Crude product was chromatographed on silica gel with EtOAc/hexanes (10 then 20%) as eluant to afford product as a colorless solid (118 mg, 70%). 1H NMR (CDCl3) 2.33 (d, J=1.3, 3H), 7.43-7.59 (m, 4 H), 7.62 (d, J=4.0, 1H), 7.80-7.83 (m, 2H). 13C NMR 7.9, 118.7 (q, J=271), 128.8, 128.9, 129.4, 133.0, 134.8, 136.3, 137.7, 145.8, 155.5 (q, J=40), 157.9, 188.0. 19F NMR −63.1. LC/MS 7.29 min, [M+1]+ 338.

Workup

customCrude product was chromatographed on silica gel with EtOAc/hexanes (10

Sources & evidence

ORD record: ord-e57fe9ec131945e7b2f9a2221463247b
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029397B2

Reaction notes

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