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Boron tribromide → 2-(4-Hydroxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester

HRID 1013037
Notes
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Reaction equation

HRID 1013037 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=2)[N:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[N:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11021617Ethyl 1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 589487762-(4-Hydroxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl esterYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 2-(4-methoxyphenyl)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (200 mg, 0.768 mmol, Example 10, Step 1) in methylene chloride (10 mL) at −40° C. was added boron tribromide (2.3 mL). The reaction was allowed to stir for 1 hour at −40° C. and for an additional hour while warming to room temperature. The reaction was quenched with ethanol diluted with water and methylene chloride. The organic layer was dried (MgSO4) and concentrated to give 128 mg of the desired product. LC-MS (C13H14N2O3 calculated 246) m/z 247 (M+H).

Workup

  1. temperaturewhile warming to room temperature
  2. customThe reaction was quenched with ethanol
  3. additiondiluted with water and methylene chloride
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3f098e1545f8466cae264c623328d1ac
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981896B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes