Carbon tetrabromide → 1-[(2E)-6-bromo-4-(4-chlorophenyl)-2,3-difluoro-2-hexenyl]-3-phenoxybenzene

HRID 1634378노트

반응식

HRID 1634378 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](/[C:12](/[F:29])=[C:13](\[F:28])/[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)[CH2:9][CH2:10]O)=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC>[Br:31][CH2:10][CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)/[C:12](/[F:29])=[C:13](\[F:28])/[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromide2회HCID 11776Triphenylphosphine2회HCID 59032878(4E)-3-(4-Chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexen-1-ol

생성물 1

HCID 590328721-[(2E)-6-bromo-4-(4-chlorophenyl)-2,3-difluoro-2-hexenyl]-3-phenoxybenzene수율 69.8%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a stirred solution of (4E)-3-(4-chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexen-1-ol (0.10 g, 0.24 mmol) in ether (5 ml) under nitrogen was added carbon tetrabromide (0.085 g, 0.256 mmol), followed by triphenylphosphine (0.067 g, 0.255 mmol), and the resulting mixture was stirred overnight at room temperature. Additional quantities of carbon tetrabromide (0.17 g, 0.51 mmol) and triphenylphosphine (0.134 g, 0.51 mmol) were added, and the reaction mixture was stirred for five hours. The reaction mixture was concentrated in vacuo and the residue chromatographed on preparative thin layer silica gel plates, developing with methylene chloride to afford the title compound as a colorless oil (0.08 g) which was characterized by 1MMR, 19FNMR and mass spectral analysis.

후처리

  1. stirringthe reaction mixture was stirred for five hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue chromatographed on preparative thin layer silica gel plates

출처 및 근거

ORD 기록
ord-9dbeb36388cb4ae5850df4da9ed1a482
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506800B2

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