Methyl iodide → 4-bromo-5-(methoxymethyl)-1-methyl-1H-pyrazole

HRID 523108

Reaction equation

HRID 523108 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[N:6][N:7]([CH3:11])[C:8]=1[CH2:9][OH:10].I[CH3:13]>C1COCC1.CN(C=O)C.C1COCC1.[Cl-].[Na+].O>[Br:3][C:4]1[CH:5]=[N:6][N:7]([CH3:11])[C:8]=1[CH2:9][O:10][CH3:13]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57415773(4-bromo-1-methyl-1H-pyrazol-5-yl)methanol

Product 1

HCID 899956044-bromo-5-(methoxymethyl)-1-methyl-1H-pyrazoleYield 67.2%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

NaH (60%, 58 mg) was added to a solution of (4-bromo-1-methyl-1H-pyrazol-5-yl)methanol (Preparation 149, 97 mg, 1.03 mmol) in THF/DMF (8/4 mL). After stirring for 15 minutes, iodomethane (439 mg, 3.09 mmol) in THF (1 mL) was added. The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with brine and extracted with EtOAc. The combined organic layers were washed with water, dried over sodium sulphate and concentrated in vacuo to afford the title compound (142 mg, 67%).

Workup

  1. stirringThe resulting solution was stirred at room temperature for 16 hours
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-07e36eea7b7d45ccb68517445ea40eec
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Linked notes

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