4-bromo-1-methyl-1H-pyrazole-5-carbaldehyde → (4-bromo-1-methyl-1H-pyrazol-5-yl)(phenyl)methanol

HRID 1485023Notes

Reaction equation

HRID 1485023 reaction equation
[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[CH:8]=[O:9].[C:10]1([Mg]Cl)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9]

Participants

4

Reactant 2

HCID 27946344-bromo-1-methyl-1H-pyrazole-5-carbaldehydeHCID 178478979HCID 178478979, compound

Product 1

HCID 14520172(4-bromo-1-methyl-1H-pyrazol-5-yl)(phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-Bromo-2-methyl-2H-pyrazole-3-carbaldehyde (1.00 g; 5.29 mmol) was dissolved in 5.0 ml of anhydrous THF and cooled down to −78° C. Phenylmagnesium chloride 2 mol/l (6.61 ml; 13.23 mmol) was dropped and stirred for 1 hour. It was warmed up to 0° C. and quenched carefully with water, then extracted with DCM. The organic layers were pooled, dried over MgSO4 and purified by using reversed phase chromatography under basic conditions.

Workup

  1. temperatureIt was warmed up to 0° C.
  2. customquenched carefully with water
  3. extractionextracted with DCM
  4. dry with materialdried over MgSO4
  5. custompurified

Sources & evidence

ORD record
ord-3122bed70f5442f8af39132a9904efc7
Source dataset
uspto-grants-2016_08
Patent number
US09422290B2

Reaction notes

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