Sodium Hydroxide → HCID 14871098, compound

HRID 2376208Notes

Reaction equation

HRID 2376208 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[CH:16][C:15]([CH2:25]O)=[N:14]2)=[CH:9][CH:8]=1.[OH-].[Na+]>C(Cl)Cl>[Br:2][CH2:25][C:15]1[CH:16]=[C:17]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[N:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH3:5])=[CH:8][CH:9]=2)[N:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 14871095HCID 14871095, compound

Product 1

HCID 14871098HCID 14871098, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phosphorus tribromide (9.31 g, 34.5 mmol) in CH2Cl2 (186 mL) was added drop-wise to a stirred solution of [1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-methanol (7.80 g, 26.5 mmol; prepared analogously to the procedure described in Step C of Example 1) in 50 mL CH2Cl2 at 0° C. The reaction mixture was stirred for an additional 18 h at rt, and then the mixture was neutralized by addition of 40% NaOH with cooling in an ice bath. The organic layer was separated and dried over Na2SO4, and solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (CH2Cl2) yielding 8.09 g (86%) of 3-bromomethyl-1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazole. HPLC: Rt=10.38. (Method A). MS (ES+): mass calculated for C18H17BrN2O, 356.05; m/z found 357.5 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.42 (s, 4H), 7.39-7.34 (m, 2H), 7.02-6.98 (m, 2H), 6.69 (s, 2H), 4.73 (s, 2H), 3.97 (s, 1H), 2.49 (s, 3H).

Workup

  1. customprepared analogously to the procedure
  2. customat 0° C
  3. temperaturewith cooling in an ice bath
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4, and solvent
  6. customwas removed under reduced pressure
  7. customThe residue was purified by silica gel chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-855b1b276806413ba6ee9728c4c2d565
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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