Triphenylphosphine dibromide → 4-(bromomethyl)-5-phenyl-3,6-dihydro-2H-pyran

HRID 1484796Notes

Reaction equation

HRID 1484796 reaction equation
[C:1]1([C:7]2[CH2:12][O:11][CH2:10][CH2:9][C:8]=2[CH2:13]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[Br:15][CH2:13][C:8]1[CH2:9][CH2:10][O:11][CH2:12][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 90417308(5-phenyl-3,6-dihydro-2H-pyran-4-yl)methanol

Product 1

HCID 904185714-(bromomethyl)-5-phenyl-3,6-dihydro-2H-pyranYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (5-phenyl-3,6-dihydro-2H-pyran-4-yl)methanol (360 mg, 1.89 mmol) in DCM (6 mL) was added dibromotriphenylphosphorane (880 mg, 2.08 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=9:1) to give 4-(bromomethyl)-5-phenyl-3,6-dihydro-2H-pyran (380 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=9:1)

Sources & evidence

ORD record
ord-73b84ea6186041fd84863220c12f42c6
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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