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

HRID 1484796
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반응식

HRID 1484796 반응식
[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
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참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-73b84ea6186041fd84863220c12f42c6
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09422279B2

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