Boron tribromide → HCID 58506493, compound

HRID 2167302Notes

Reaction equation

HRID 2167302 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[N:11]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:12]1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[N:11]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:12]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58506460HCID 58506460, compound

Product 1

HCID 58506493HCID 58506493, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-(2,4-dimethoxyphenyl)-1H-pyrazole-3-carboxylate 2 (1.00 g, 3.82 mmol, 1.00 equiv) in DCM (20 mL) was added BBr3 (9.55 g, 38.2 mmol, 10 equiv) at −40° C. The resulting solution was stirred overnight at room temperature. The mixture was quenched by the addition of 10 mL of water and the reaction mixture was extracted with 3×200 mL of ethyl acetate. The combined organic layers were washed with 200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.8 g (90%) of methyl 1-(2,4-dihydroxyphenyl)-1H-pyrazole-3-carboxylate 3 as a white solid. LC-MS: m/z=235 (MH)+.

Workup

  1. customThe mixture was quenched by the addition of 10 mL of water
  2. extractionthe reaction mixture was extracted with 3×200 mL of ethyl acetate
  3. washThe combined organic layers were washed with 200 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 0.8 g (90%) of methyl 1-(2,4-dihydroxyphenyl)-1H-pyrazole-3-carboxylate 3 as a white solid

Sources & evidence

ORD record
ord-8341d5cad6b94da699c88eeaf12dd682
Source dataset
uspto-grants-2015_06
Patent number
US09045440B2

Reaction notes

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