Boron tribromide → 3-methyl-4-[4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazol-3-yl]phenol

HRID 1784485Notes

Reaction equation

HRID 1784485 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([CH3:18])[C:16]([C:19]34[CH2:26][CH2:25][C:22]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH2:23][CH2:24]3)[CH2:21][CH2:20]4)=[N:15][N:14]=2)=[C:9]([CH3:32])[CH:8]=1>C(Cl)Cl>[CH3:32][C:9]1[CH:8]=[C:7]([OH:6])[CH:12]=[CH:11][C:10]=1[C:13]1[N:17]([CH3:18])[C:16]([C:19]23[CH2:24][CH2:23][C:22]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH2:25][CH2:26]2)[CH2:21][CH2:20]3)=[N:15][N:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 103624513-(4-methoxy-2-methylphenyl)4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)4H-1,2,4-triazole

Product 1

HCID 1355436643-methyl-4-[4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazol-3-yl]phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1M/CH2Cl2, 3.21 mL, 3.21 mmol) was added to a solution of 3-(4-methoxy-2-methylphenyl)4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)-4H-1,2,4-triazole (2-F) (410 mg, 1.07 mmol) in methylene chloride (6 mL) at 0° C. The mixture was stirred at room temperature for 2 h. The solution was washed with water, 10% NaHCO3, dried (MgSO4) and concentrated in vacuo. The residue was purified by preparative TLC (silica gel, MeOH:methylene chloride, 5:95) to provide 3-methyl-4-[4-methyl-5-(4-pentylbicyclo[2.2.2]oct-1-yl)4H-1,2,4-triazol-3-yl]phenol (2-G). Mass spectrum: 393 (M+1); 1H NMR (500 MHz, CDCl3): δ 0.93 (t, 3H); 1.27 (m, 8H); 1.56 (m, 6H); 1.97 (s 3H); 2.12 (m, 6H); 3.50 (s, 3H); 6.65 (m, 2H); 6.98 (d, 1H) ppm.

Workup

  1. washThe solution was washed with water, 10% NaHCO3
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative TLC (silica gel, MeOH:methylene chloride, 5:95)

Sources & evidence

ORD record
ord-b1c506f5bd4a4f69afabbbdda5d1ebd2
Source dataset
uspto-grants-2009_03
Patent number
US07504402B2

Reaction notes

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