Phosphorus tribromide → HCID 90112431, compound

HRID 1508885Notes

Reaction equation

HRID 1508885 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][CH:9]=2)[CH:6]=1.P(Br)(Br)[Br:17]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Br:17][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:5]2[CH:6]=[C:2]([Cl:1])[CH:3]=[N:4]2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 90112556HCID 90112556, compound

Product 1

HCID 90112431HCID 90112431, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of (4-((4-chloro-1H-pyrazol-1-yl)methyl)phenyl)methanol (0.375 g, 1.68 mmol) in methylene chloride (7 mL) at 0° C. under a nitrogen atmosphere was treated with PBr3 (0.456 g, 1.68 mmol) and the mixture was warmed to rt and stirred for 1 h. After this time, the mixture was diluted with saturated aqueous sodium bicarbonate and ice and then extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/dichloromethane) to afford the title compound (0.342 g, 91%) as a white solid. MW=285.57. 1H NMR (CDCl3, 500 MHz) δ 7.46 (s, 1H), 7.38 (d, J=8.1 Hz, 2H), 7.35 (s, 1H), 7.19 (d, J=8.1 Hz, 2H), 5.24 (s, 2H), 4.47 (s, 2H).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silica, hexanes/dichloromethane)

Sources & evidence

ORD record
ord-ae6a4cc6532d45b9a062a5d081ef9972
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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