1-Bromo-4-isopropylbenzene → HCID 21846687, Verbindung

HRID 619653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619653
[CH:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C([Li])(C)(C)C.[CH3:16][C:17]1([CH3:48])[CH:26]=[C:25](OS(C(F)(F)F)(=O)=O)[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:35]#[C:36][C:37]3[CH:47]=[CH:46][C:40]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:39][CH:38]=3)[CH:23]=2)[O:18]1>C1COCC1.CCCCC.[Cl-].[Cl-].[Zn+2].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:2][CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:35]#[C:36][C:37]4[CH:47]=[CH:46][C:40]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:39][CH:38]=4)[CH:23]=3)[O:18][C:17]([CH3:16])([CH3:48])[CH:26]=2)=[CH:6][CH:5]=1)[CH3:3]

Komponenten

8

Edukt 3

HCID 114621-Bromo-4-isopropylbenzeneHCID 21846667HCID 21846667, Verbindung2×HCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 21846687HCID 21846687, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 3007855ZincchlorideKatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 4-iso-propylbromobenzene (250.0 mg, 1.25 mmol) in 3.0 mL of THF was cooled to -78° C. and tert-butyllithium (160.8 mg, 2.51 mmol, 1.5 ml of a 1.7M solution in pentane) was added to give a yellow solution. After 30 minutes a solution of ZnCl2 (345.0 mg, 2.53 mmol) in 5.0 mL THF was slowly added via cannula. The resulting solution was warmed to room temperature and transferred via cannula to a solution of ethyl 4-((2,2-dimethyl-4-trifluoromethanesulfonyloxy-(2H)-chromen-6-yl)ethynyl)-benzoate (Compound 264, 150.0 mg, 0.31 mmol) and tetrakis(triphenylphosphine) palladium(0) (24.0 mg, 0.02 mmol) in 2.0 mL THF. This solution was heated to 50° C. for 2 hours, cooled to room temperature, and the reaction quenched by the addition of saturated aqueous NH4Cl. This solution was extracted with EtOAc and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound, 100.0 mg (72%), was isolated by column chromatography (2.5% EtOAc/hexanes) as a colorless solid. 1H NMR (300 MHz, CDCl3) δ: 7.99 (2H, d, J=8.3 Hz), 7.52 (2H, d, J=8.3 Hz), 7.36 (1H, dd, J=2.1, 8.3 Hz), 7.30-7.26 (5H, m), 6.88 (1H, d, J=8.3 Hz), 5.64 (1H, s), 4.38 (2H, q, J=7.1 Hz), 2.98 (1H, hept, J=7.0 Hz), 1.51 (6H, s), 1.40 (3H, t, J=7.1 Hz), 1.31 (6H, d, J=7.0 Hz).

Aufarbeitung

  1. customto give a yellow solution
  2. temperatureThis solution was heated to 50° C. for 2 hours
  3. temperaturecooled to room temperature
  4. customthe reaction quenched by the addition of saturated aqueous NH4Cl
  5. extractionThis solution was extracted with EtOAc
  6. washthe combined organic layers were washed with H2O and saturated aqueous NaCl
  7. dry with materialbefore being dried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-84eaf445fff84455bf3c9f3a6d222b32
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958954

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