2,7-Dibromo-9-(bis-methylsulfanyl-methylene)fluorene → 2,7-Dibromo-9-(bisoctyl-methylene)fluorene

HRID 496320

반응식

HRID 496320 반응식
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5](=[C:16](SC)SC)[C:4]=2[CH:3]=1.[CH2:21]([Mg]Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5](=[C:16]([CH2:13][CH2:14][CH2:2][CH2:3][CH2:4][CH2:12][CH2:11][CH3:10])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:4]=2[CH:3]=1

참가 물질

5

반응물 2

HCID 121516122,7-Dibromo-9-(bis-methylsulfanyl-methylene)fluoreneHCID 178443577HCID 178443577, 화합물

생성물 1

HCID 121516162,7-Dibromo-9-(bisoctyl-methylene)fluorene

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
5 °C

실험 절차

To a solution of 2,7-dibromo-9-(bis-methylsulfanyl-methylene)fluorene (5.1 g, 12 mmol) in dry THF (100 ml) at 0° C. under nitrogen, was added a solution of lithium tetrachlorocuprate (5 ml of a 0.1 M solution in THF, 5 mol %). A solution of octylmagnesium bromide (13 ml of a 2.0M solution in diethyl ether, 0.026 mol) was added dropwise over 30 min. The reaction was stirred for 2 h at 5° C. The reaction was cooled to 0° C. and further lithium tetrachlorocuprate (1 ml of a 0.1M solution in THF, 1 mol %) was added. The reaction was then stirred for 24 h at 15° C., before quenching and workup as above. Yield (60%). Purity (HPLC>99%). 1H and 13C NMR spectra as expected. M+=560 (t).

후처리

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringThe reaction was then stirred for 24 h at 15° C.
  3. custombefore quenching
  4. customYield (60%)

출처 및 근거

ORD 기록
ord-a5ba07bf6a4d4964add042633a80500c
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943275B2

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