Benzoic acid, 4-[5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl- synthesis
- Product Name:Benzoic acid, 4-[5-(3,5-dichloro-4-fluorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-
- CAS Number:1332698-41-5
- Molecular formula:C18H11Cl2F4NO3
- Molecular Weight:436.18
![Benzoic acid, 4-[chloro(hydroxyimino)methyl]-2-methyl-](/CAS/20210305/GIF/1437051-96-1.gif)
Yield:1332698-41-5 58%
Reaction Conditions:
with triethylamine in N,N-dimethyl-formamide at 0 - 20; for 18 h;
Steps:
1.8.4 Step 4:
Step 4:
Preparation of 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid
To a solution of 4-(chloro(hydroxyimino)methyl)-2-methylbenzoic acid (5.1 g, 23.8 mmol) in DMF (30 mL) at 0° C. was added 1,3-dichloro-2-fluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (7.4 g, 28.6 mmol) followed by Et3N (4.8 g, 47.6 mmol).
The reaction mixture was stirred at rt for 18 h, poured into ice-water (30 mL) and extracted with ethyl acetate (60 mL*3).
The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure.
The residue was purified by column chromatography over silica gel eluted with PE:EA (1:1) to EA: MeOH (10:1) to give 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid (6 g; yield 58% over 3 steps) as a white solid. MS: m/z=435.8 (M+1, ESI+).
References:
US2013/131017,2013,A1 Location in patent:Paragraph 0299
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