Sodium Hydroxide → HCID 59355029, compound

HRID 2196423Notes

Reaction equation

HRID 2196423 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=1)[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59354987HCID 59354987, compound

Product 1

HCID 59355029HCID 59355029, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-bromo-4-(1-methyl-1H-pyrazol-5-yl)benzoate (275 mg, 0.93 mmol) in MeOH (10 mL) was added NaOH solution (2.5 M, 3.72 mL, 9.3 mmol). After 12 h at 25° C., the solution was partitioned between H2O-DCM and the pH of the aqueous phase was adjusted to ˜4 with 6N HCl solution. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4 and concentrated to afford the title compound as a white solid (230.1 mg, 88%): LC-MS (ES) m/z=282 (M+H)+.

Workup

  1. customthe solution was partitioned between H2O-DCM
  2. washThe aqueous phase was washed several times with DCM
  3. dry with materialthe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d89aef69656a464982c2e6d7d7ae68f4
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

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