Triphenylphosphine dibromide → 5-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazole

HRID 1770802Notes

Reaction equation

HRID 1770802 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[CH2:14][O:13][CH2:12][CH2:11][C:10]=2[CH2:15]O)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[Br:17]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[Br:17][CH2:15][C:10]1[CH2:11][CH2:12][O:13][CH2:14][C:9]=1[C:8]1[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 90408368(5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methanol

Product 1

HCID 904080795-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazoleYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methanol (300 mg, 1.35 mmol) in DCM (5 mL) was added dibromotriphenylphosphorane (630 mg, 1.35 mmol) at room temperature, after stirring for 30 min, it was diluted with DCM, organic layer was washed with Sat. NaHCO3, brine, dried and concentrated to give crude product, which was purified by column (Hexanes/EtOAc=4:1) to give 5-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazole (360 mg).

Workup

  1. washwas washed with Sat. NaHCO3, brine
  2. customdried
  3. concentrationconcentrated
  4. customto give crude product, which
  5. customwas purified by column (Hexanes/EtOAc=4:1)

Sources & evidence

ORD record
ord-d6d54745e3704dcabb39ad12cc46702d
Source dataset
uspto-grants-2016_02
Patent number
US09248199B2

Reaction notes

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