Boron tribromide → HCID 136350249, compound

HRID 1410174Notes

Reaction equation

HRID 1410174 reaction equation
[CH:1]([C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)[C:4]=1[C:17]1[C:18]([CH3:27])=[C:19]([C:23]([O:25]C)=[O:24])[O:20][C:21]=1[CH3:22])=[O:2].B(Br)(Br)Br>C(Cl)Cl>[CH:1]([C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[C:4]=1[C:17]1[C:18]([CH3:27])=[C:19]([C:23]([OH:25])=[O:24])[O:20][C:21]=1[CH3:22])=[O:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86668985HCID 86668985, compound

Product 1

HCID 136350249HCID 136350249, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

methyl 4-(5-formyl-3-(4-methoxyphenyl)-1-methyl-1H-pyrazol-4-yl)-3,5-dimethylfuran-2-carboxylate (55 mg, 0.15 mmol) was dissolved in CH2Cl2 (7.5 mL) and BBr3 (1 M solution on DCM, 0.75 mL, 0.75 mmol) was added and stirred at room temperature over night. The reaction was quenched using water and extracted with CH2Cl2. Concentration and filtration trough a short plug of silica gave 4-(5-formyl-3-(4-hydroxyphenyl)-1-methyl-1H-pyrazol-4-yl)-3,5-dimethylfuran-2-carboxylic acid (45 mg, 75%) which was used as such in the next step.

Workup

  1. customThe reaction was quenched
  2. extractionextracted with CH2Cl2
  3. concentrationConcentration and filtration trough a short plug of silica

Sources & evidence

ORD record
ord-67ba7d45837f40d3beeeda5145dee6b5
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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