Boron Trichloride → HCID 136049315, compound

HRID 1296958Notes

Reaction equation

HRID 1296958 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[C:28]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[C:27]([Br:37])[NH:26][N:25]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>ClCCl>[Br:37][C:27]1[NH:26][N:25]=[C:24]([C:10]2[CH:11]=[C:12]([Cl:23])[C:13]([OH:15])=[CH:14][C:9]=2[OH:8])[C:28]=1[C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 58913505HCID 58913505, compound

Product 1

HCID 136049315HCID 136049315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(2,4-Bis-benzyloxy-5-chloro-phenyl)-5-bromo-4-(4-methoxy-phenyl)-1H-pyrazole (1 eq) was dissolved in anhydrous dichloromethane, and under a nitrogen atmosphere, was cooled to 0° C. 1M boron trichloride in dichloromethane (8 eq) was added drop wise and the solution was stirred at 0° C. for 30 minutes. The solution was added drop wise to sat. NaHCO3(aq), and extracted into dichloromethane. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated in vacuo, to give a white solid. This was purified by preparative LC/MS to give 4-[5-bromo-4-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-6-chloro-benzene-1,3-diol (Example 179) as a white solid.

Workup

  1. extractionextracted into dichloromethane
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a white solid
  7. customThis was purified by preparative LC/MS

Sources & evidence

ORD record
ord-98984905032043e7bf653297e7f5976a
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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