Methyl 4-bromo-1-methyl-1H-pyrazole-5-carboxylate → (4-bromo-1-methyl-1H-pyrazol-5-yl)methanol

HRID 58036

Reaction equation

HRID 58036 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH3:11])[C:6]=1[C:7](OC)=[O:8].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH3:11])[C:6]=1[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 673643Methyl 4-bromo-1-methyl-1H-pyrazole-5-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 57415773(4-bromo-1-methyl-1H-pyrazol-5-yl)methanolYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 4-bromo-1-methyl-1H-pyrazole-5-carboxylate (2 g, 9.13 mmol) in DCM (40 mL) was cooled to −78° C. Diisobutylaluminum hydride (36.5 mL, 36.5 mmol) in DCM was added, and the reaction mixture was stirred for 2 hours at the same temperature. The reaction mixture was subsequently quenched with aqueous saturated sodium potassium tartrate and was transferred to a reparatory funnel, where it was washed with water and brine, dried over Na2SO4, and concentrated to give the title compound as a white solid (0.76 g, 44%).

Workup

  1. customThe reaction mixture was subsequently quenched with aqueous saturated sodium potassium tartrate
  2. customwas transferred to a reparatory funnel
  3. washwhere it was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-97d9fef71a1c42feaeba9123a32dd627
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Linked notes

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