Triphenylphosphine → HCID 10754143, compound

HRID 343132Notes

Reaction equation

HRID 343132 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[CH2:22]([N:29]1[C:33]([CH2:34]O)=[CH:32][C:31]([CH3:36])=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl>[CH2:22]([N:29]1[C:33]([CH2:34][Br:20])=[CH:32][C:31]([CH3:36])=[N:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24408BromineHCID 516892Sodium BicarbonateHCID 10512304HCID 10512304, compound

Product 1

HCID 10754143HCID 10754143, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 1.10 g (4.21 mmol, 1.2 equiv) of triphenylphosphine in 15 mL of CCl4 at -5° C. is added 200 μL (3.86 mmol, 1.1 equiv) of Br2. The resulting orange-yellow suspension is stirred 10 min at 0° C., then a solution of 710 mg (3.51 mmol) of (2-Benzyl-5-methyl-2H-pyrazol-3yl) methanol, prepared as in Part C, in 5 mL of CCl4 is added over 2 min. The resulting solution is stirred 0.5 h at RT, and then poured into 25 mL NaHCO3 and extracted with Et2O (2×25 mL), dried (MgSO4), and the solvent removed in vacuo. Purification of the residue by silica gel flash column chromatography using hexane/EtOAc 5/1 as eluent afforded 576 mg of the title compound as a clear oil: 1H NMR (CDCl3, 300 MHz) δ7.32 (m, 3H), 7.19 (m, 2H), 6.16 (s, 1H), 5.42 (s, 2H), 4.32 (s, 2H), 2.31 (s, 3H); low resolution MS (FAB)m/e 265 (M+).

Workup

  1. stirringThe resulting solution is stirred 0.5 h at RT
  2. extractionextracted with Et2O (2×25 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customPurification of the residue by silica gel flash column chromatography

Sources & evidence

ORD record
ord-90658de25d924b3facf94cb719ea5c2a
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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