1,2-Dibromobenzene → HCID 57801671, Verbindung

HRID 2101527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2101527
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[Li]CCCC.Cl[Sn:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19]>C1COCC1.CCCCCC>[Br:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Sn:15]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:16][CH2:17][CH2:18][CH3:19]

Komponenten

6

Edukt 3

HCID 114141,2-DibromobenzeneHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Produkt 1

HCID 57801671HCID 57801671, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A microsystem composed of three T-shaped micromixers (M1, M2 and M3) and two microtube reactors (R1 and R2) was used. The whole microsystem was dipped in a cooling bath (−78° C.). A solution of o-dibromobenzene (0.27 M) in THF (flow rate: 6 mL/min, 1.62 mmol/min) and a solution of n-BuLi (1.5 M) in n-hexane (flow rate: 1.2 mL/min, 1.8 mmol/min) were introduced to the first T-shaped mixer M1 (inner diameter: 250 μm) by using syringe pumps. The resulting solution was passed through the tube reactor R1 and was mixed with chlorotributylstannane (Bu3SnCl) (0.32 M) in THF (flow rate: 6 mL/min, 1.92 mmol/min) in the second T-shaped mixer M2 (inner diameter: 500 μm). The resulting solution was passed through the tube reactor R2 and was introduced to the third T-shaped mixer M3 (inner diameter: 500 μm), where the solution was quenched with methanol (neat, flow rate=3.0 mmol/min). The residence time of the tube reactor R1 (inner diameter: 500 μm, length=50 cm) was 0.82 second. The residence time of the tube reactor R2 (inner diameter: 1,000 μm, length=50 cm) was 1.78 second. After finishing the reaction, an aliquot of the product solution was taken (15 sec) and was concentrated, then the residue was subjected to silica gel column chromatography (hexane) to refine, 2-bromophenyltributylstannane was obtained as colorless oil in 81% yield, 146.6 mg. 1H NMR (400 MHz, CDCl3) δ: 0.88 (t, J=7.2 Hz, 9H), 1.12-1.17 (m, 6H), 1.27-1.38 (m, 6H), 1.51-1.60 (m, 6H), 7.10-7.15 (dt, J=7.6, 1.6 Hz, 1H), 7.18-7.23 (dt, J=7.6, 1.2 Hz, 1H), 7.27-7.31 (dd, J=7.6, 1.6 Hz, 1H), 7.44-7.50 (dd, J=7.6, 1.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ: 11.0, 13.8, 27.4, 29.1, 126.1, 129.8, 131.5, 133.2, 137.8, 146.5. HRMS (EI) m/z: calcd. for C14H22BrSn (M+-C4H9) 388.9927, found 388.9925.

Aufarbeitung

  1. customThe whole microsystem was dipped in a cooling bath
  2. custom(−78° C.)
  3. additionwas introduced to the third T-shaped mixer M3 (inner diameter: 500 μm), where the solution
  4. customwas quenched with methanol (neat, flow rate=3.0 mmol/min)
  5. waitThe residence time of the tube reactor R2 (inner diameter: 1,000 μm, length=50 cm) was 1.78 second
  6. customthe reaction
  7. custom(15 sec)
  8. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7aa18e2d27f04ff98d7069f85ddf6a95
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572927B2

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