Dichloromethane → HCID 67409996, compound

HRID 1191177Notes

Reaction equation

HRID 1191177 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[N:8]=[C:9]([C:11]([CH3:15])([CH3:14])[CH2:12][F:13])[CH:10]=1)=[O:5])[CH3:2].C(Cl)[Cl:18]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[N:8]=[C:9]([C:11]([CH3:15])([CH3:14])[CH2:12][F:13])[C:10]=1[Cl:18])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 67412034HCID 67412034, compound

Product 1

HCID 67409996HCID 67409996, compound

Procedure

5-(2-fluoro-1,1-dimethyl-ethyl)-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (722 mg, 3.16 mmol, prepared as described in the previous step) was dissolved in DCM (5 mL) and SO2Cl2 (0.256 mL, 3.16 mmol) was added dropwise to the stirred solution. The resulting mixture was stirred at room temperature for 16 h and then the solvent was removed under reduced pressure. The resulting residue was chromatographed on a 40-g SiO2 pre-packed column eluting with 0:1-1:4 EtOAc/heptane to yield 4-chloro-5-(2-fluoro-1,1-dimethyl-ethyl)-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester. 1H-NMR (400 MHz, CDCl3) δ: 4.59 (d, J=47 Hz, 2H), 4.40 (q, J=7.1 Hz, 2H), 4.08 (s, 3H), 1.43 (d, J=1.7 Hz, 6H), 1.41 (t, J=7.2 Hz, 3H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe resulting residue was chromatographed on a 40-g SiO2 pre-packed column
  3. washeluting with 0:1-1:4 EtOAc/heptane

Sources & evidence

ORD record
ord-3348079ef983430c93d28107f6be18a4
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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