Phosphorus tribromide → HCID 67251280, compound

HRID 41589Notes

Reaction equation

HRID 41589 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH2:13]O)[CH:10]=[CH:11][CH:12]=1.P(Br)(Br)[Br:16]>C1COCC1>[Br:16][CH2:13][C:9]1[CH:8]=[C:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 53425549(3-(Pyrazin-2-YL)phenyl)methanol

Product 1

HCID 67251280HCID 67251280, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (3-(pyrazin-2-yl)phenyl)methanol (200 mg, 1.08 mmol) in THF (5 mL), PBr3 (349 mg, 1.29 mmol) was added dropwise at 0° C. and stirred for 10 min. Then, the reaction mixture was refluxed for 3 h. The mixture was cooled to rt, poured into ice-cold saturated aqueous NaHCO3 solution (5 mL) and extracted with ethyl acetate (2×). The combined organic layers were washed with brine and dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield the title compound (200 mg, 75%). [TLC Rf=0.54 (ethyl acetate/hexane 50:50)].

Workup

  1. temperatureThen, the reaction mixture was refluxed for 3 h
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11c4b9d0a2384d43b6b2b2b1e47c17f4
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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