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Diethyl Ether → HCID 67204228, 화합물

HRID 1036812
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HRID 1036812 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOCC>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][Br:20])=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 672034892-(4-(Benzyloxy)-3-fluorophenyl)ethanol

생성물 1

HCID 67204228HCID 67204228, 화합물수율 93.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(4-benzyloxy-3-fluoro-phenyl)-ethanol (1.0 g, 4.0 mmol) and CBr4 (1.5 g, 4.5 mmol) in CH2Cl2 (10 mL), was PPh3 (1.2 g, 4.5 mmol) added portionwise at 0° C. The reaction mixture stirred for 2 hours at the same temperature. The reaction was concentrated under vacuum and the residue was stirred in ether (10 mmol). The solid, mainly triphenylphosphine oxide, was filtrated off and the filtrate was concentrated under vacuum. The residue was purified over SiO2 to afford the desired compound (1.15 g, 93.5%) as a white crystal. 1H NMR (400 MHz, DMSO-d6) δ 7.36-7.49 (m, 5H), 7.17-7.23 (m, 2H), 7.03-7.05 (m, 1H), 5.18 (s, 2H), 3.72 (t, 2H), 3.08 (t, 2H). LCMS 273.4 [MH+].

후처리

  1. additionadded portionwise at 0° C
  2. concentrationThe reaction was concentrated under vacuum
  3. filtrationThe solid, mainly triphenylphosphine oxide, was filtrated off
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was purified over SiO2

출처 및 근거

ORD 기록
ord-69fcf040dd564316b098d2f5e8cf1134
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546429B2

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