Hydrochloric Acid → HCID 67482917, compound

HRID 1715513Notes

Reaction equation

HRID 1715513 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([O-:5])=O.[K+].[Mg+2].[Cl-].[Cl-].C(N(CC)CC)C.[F:21][C:22]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:23]=1C(Cl)=O.Cl>C(OCC)(=O)C>[F:21][C:22]1[CH:23]=[CH:27][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:29][C:30]=1[C:3](=[O:5])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl ChlorideHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium Chloride

Product 1

HCID 67482917HCID 67482917, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

Potassium ethyl malonate (10.2 g, 60 mmol), MgCl2 (6.3 g, 66 mmol), and triethylamine (28 ml, 200 mmol) were suspended in dry ethyl acetate (200 ml) and heated to 40° C. for 15 hr. A solution of 2-fluoro-5-trifluoromethylbenzoyl chloride (10 g, 44.1 mmol) in ethyl acetate (40 ml) was dropped in slowly (in about one hour). After another hour, the mixture was treated with 2N HCl (200 ml). The organic layer was washed with 0.5 N HCl 2×, 5% K2CO3 2×, brine 2×, and dried over Na2SO4. Evaporation of the solvent and vacuum drying afforded ethyl 3-[2-fluoro-5-(trifluoromethyl)phenyl]-3-oxopropanoate as a pale yellow oil. NMR (500 MHz, CDCl3) δ: 1.25 (t, J=7.4 Hz, 3H); 1.32*; 4.00 (d, JF-H=3 Hz, 2H); 4.21 (q, J=7.4 Hz, 2H); 5.8*; 7.22*; 7.29 (t, J=10.3 Hz, 1H); 7.66*; 7.82 (br, 1H); 8.14*; 8.24 (d, J=6.4 Hz, 1H). Enol form* exists in about 35%.

Workup

  1. waitAfter another hour
  2. washThe organic layer was washed with 0.5 N HCl 2×, 5% K2CO3 2×, brine 2×
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent and vacuum
  5. customdrying

Sources & evidence

ORD record
ord-2b3e21b6ba2b4853834ec92152649b1c
Source dataset
uspto-grants-2010_09
Patent number
US07799818B2

Reaction notes

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