Chloromethyl Methyl Ether → HCID 58223402, compound

HRID 41265Notes

Reaction equation

HRID 41265 reaction equation
[O:1]1[CH2:5]CC[CH2:2]1.[Br:6][C:7]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([Br:17])[NH:9][N:8]=1.C(N(CC)C(C)C)(C)C.COCCl>O>[Br:17][C:10]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]([Br:6])[N:8]([CH2:2][O:1][CH3:5])[N:9]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 24799525Ethyl 3,5-dibromo-1H-pyrazole-4-carboxylate

Product 1

HCID 58223402HCID 58223402, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a tetrahydrofuran (262 mL) solution of ethyl 3,5-dibromo-1H-pyrazole-4-carboxylate (20.93 g, 703 mmol) was added N,N-diisopropylethylamine (24.5 mL, 141 mmol), and chloromethyl methyl ether (6.42 mL, 84.3 mmol) was added dropwise while cooling on ice, and stirred at room temperature for one hour. After the reaction was completed, water was added while cooling on ice, the reaction mixture was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate=3/1) to obtain the title compound (23.4 g, 68.5 mmol).

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling on ice
  3. temperaturewhile cooling on ice
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-heptane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-2f528e5a89ec40e986b57e3e89669edc
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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