Phosphorus tribromide → 2-(2-(Bromomethyl)phenyl)-2H-1,2,3-triazole

HRID 41583Notes

Reaction equation

HRID 41583 reaction equation
[N:1]1[N:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12]O)[N:3]=[CH:4][CH:5]=1.P(Br)(Br)[Br:15].C([O-])(O)=O.[Na+]>C1COCC1>[Br:15][CH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[N:2]1[N:3]=[CH:4][CH:5]=[N:1]1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 67251671(2-(2H-1,2,3-Triazol-2-YL)phenyl)methanol

Product 1

HCID 672510032-(2-(Bromomethyl)phenyl)-2H-1,2,3-triazoleYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of (2-(2H-1,2,3-triazol-2-yl)phenyl)methanol (37 mg, 0.209 mmol) in THF (1 mL), PBr3 (0.024 mL, 0.251 mmol) was added and the mixture was heated at 70° C. for 20 min. The mixture was cooled to rt, poured into saturated aqueous NaHCO3 solution and extracted with dichloromethane (2×). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane) to yield the title compound (28 mg, 54%). [1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.17 (s, 2H), 7.69 (ddd, J=7.59, 3.58, 1.63 Hz, 2H), 7.53 (dqd, J=14.74, 7.51, 7.51, 7.51, 1.63 Hz, 2H), 4.96 (s, 2H); LCMS RtA=1.02, [M+H]+=238.2/240.2].

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionextracted with dichloromethane (2×)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-cc2b170f36ab4b2dbe45340678ae088f
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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