Boron tribromide → HCID 21915373, compound

HRID 1787526Notes

Reaction equation

HRID 1787526 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[S:17][CH:16]=[CH:15][C:11]=3[N:12]([CH3:14])[N:13]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>ClCCl>[CH3:14][N:12]1[C:11]2[CH:15]=[CH:16][S:17][C:10]=2[C:9]([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)=[N:13]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 140972473-(3-methoxyphenyl)-1-methyl-1H-thieno[3,2-c]pyrazole

Product 1

HCID 21915373HCID 21915373, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a stirred solution of 3-(3-methoxyphenyl)-1-methyl-1H-thieno[3,2-c]pyrazole (7.5 g, 0.031 mol.) and dichloromethane (51 mL) dropwise with a solution of boron tribromide (41 mL, 0.041 mol., 1.0M in dichloromethane) under nitrogen. After 2.5 hours, quench with hydrochloric acid (50 mL, 1N) and ether/ethyl acetate (50 mL), and stir until both phases are clear. Wash the organic phase with water, dry (MgSO4), filter and evaporate to give an oil. Purify the oil by HPLC (silica gel, elution with 10% methanol in dichloromethane) to give a light tan solid. Purify the solid further by column chromatography (silica gel, elution with 5% methanol in dichloromethane) to give a white solid (3.5 g, 49% yield).

Workup

  1. customquench with hydrochloric acid (50 mL, 1N) and ether/ethyl acetate (50 mL)
  2. washWash the organic phase with water
  3. dry with materialdry (MgSO4)
  4. filtrationfilter
  5. customevaporate
  6. customto give an oil
  7. customPurify the oil
  8. washby HPLC (silica gel, elution with 10% methanol in dichloromethane)
  9. customto give a light tan solid
  10. customPurify the solid
  11. washfurther by column chromatography (silica gel, elution with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7da6961d5287422e8b23f8f3dbe58c8f
Source dataset
uspto-grants-2009_03
Patent number
US07511046B2

Reaction notes

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