Diethyl Ether → HCID 86666501, compound

HRID 1426341Notes

Reaction equation

HRID 1426341 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=1)C(OCC)=O.[CH3:17][Mg]Br.C([O:22][CH2:23][CH3:24])C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:23]([OH:22])([CH3:24])[CH3:17])[CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[N:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 71433010Ethyl 2-chloro-6-(trifluoromethyl)isonicotinateHCID 178418573HCID 178418573, compound

Product 1

HCID 86666501HCID 86666501, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-chloro-6-(trifluoromethyl)isonicotinate (0.200 g, 0.789 mmol, Anichem) in tetrahydrofuran (5 mL) at 0° C. was added 3.0M methylmagnesium bromide in diethyl ether (0.66 mL, 2.0 mmol). After 30 minutes, the reaction was quenched by the addition of saturated ammonium chloride solution and extracted with three portions of ethyl acetate. The combined extracts were dried over sodium sulfate, decanted and concentrated. Used without further purification in Step B. 1H NMR (300 MHz, CDCl3) δ 7.70 (d, J=1.4 Hz, 1H), 7.66-7.59 (m, 1H), 1.59 (s, 6H); 19F NMR (282 MHz, CDCl3) 5-68.30 (s); LCMS (M+H)+: 240.1.

Workup

  1. customthe reaction was quenched by the addition of saturated ammonium chloride solution
  2. extractionextracted with three portions of ethyl acetate
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. customdecanted
  5. concentrationconcentrated
  6. customUsed without further purification in Step B

Sources & evidence

ORD record
ord-3818efb1b331407680cea25926ce6ea3
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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