Boron tribromide → 3-((4-Bromo-1H-pyrazol-1-yl)methyl)phenol

HRID 2175287Notes

Reaction equation

HRID 2175287 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14]C)[CH:9]=2)[CH:6]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 551371064-Bromo-1-(3-methoxybenzyl)-1H-pyrazole

Product 1

HCID 709829143-((4-Bromo-1H-pyrazol-1-yl)methyl)phenolYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromo-1-(3-methoxybenzyl)-1H-pyrazole (3.8 g, 14.23 mmol) was dissolved in CH2Cl2 (30 mL) at 0° C. was added boron tribromide (2.69 mL, 28.5 mmol). The reaction mixture was stirred at 0° C. for 30 min and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (2.55 g, 71% yield) as a yellow oil. LCMS, [M+H]+=253.0. 1H NMR (400 MHz, CDCl3) δ 7.47 (s, 1H), 7.38 (s, 1H), 7.19 (t, J=8.0 Hz, 1H), 6.76 (d, J=8.0 Hz, 2H), 6.59 (s, 1H), 5.20 (s, 2H).

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-0578197363a64406a7cc8a1e7fbacd59
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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