2-碘-4-溴苯甲醚

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 4-bromo-2-iodo-1-methoxybenzene (Preparation 57, 350 mg, 1.12 mmol), 2-(4-(ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 21, 365 mg, 1.12 mmol) and aqueous caesium carbonate solution (1M, 2.23 mL, 2.23 mmol) in dioxane (18 mL) was degassed with nitrogen for 10 min, followed by addition of 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (46.0 mg, 0.0056 mmol). The resulting mixture was heated at 80° C. for 16 hours. After cooling to room temperature and concentration in vacuo, the crude residue was partitioned between water (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2×20 mL). The organic layers were combined and washed with brine (25 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with heptanes/EtOAc (70:30), to afford the title compound as off-white solid in 45% yield, 150 mg. After cooling to room temperature concentration in vacuo the crude residue was partitioned between water (30 mL) and EtOAc (30 mL) The aqueous layer was extracted with EtOAc (2×20 mL) washed with brine (25 mL) dried over MgSO4 concentrated in vacuo The residue was purified by silica gel column chromatography eluting with heptanes/EtOAc (70:30)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Iodomethane (103 μL, 1.65 mmol) was added to a solution of 4-bromo-2-iodophenol (450 mg, 1.51 mmol) and potassium carbonate (271 mg, 1.96 mmol) in acetone (10 mL). The resulting mixture was stirred at room temperature for 16 hours.

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-Bromo-2-iodo-1-methoxybenzene (6.07 g, 19.40 mmol), (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (5.066 g, 16.16 mmol), Pd2(dba)3 (0.370 g, 0.404 mmol), Xntphos (0.468 g, 0.808 mmol) and cesium carbonate (7.37 g, 22.63 mmol) were combined in CPME (32.3 ml) and the reaction was heated to 90° C. overnight. The reaction was cooled to RT, diluted with EtOAc and filtered over a pad of Celite (washing with EtOAc). The filtrate was concentrated in vacuo and the crude oil was then taken up in DCM and purified via MPLC, eluting with 0-20% ethyl acetate in heptanes to yield (E)-ethyl 3-(5-(benzylthio)-2-((5-bromo-2-methoxyphenyl)amino)phenyl)acrylate (6.92 g, 13.88 mmol, 86% yield) as a yellow solid. MS (ESI, pos. ion) m/z: [M+1] 498.0 The reaction was cooled to RT filtered over a pad of Celite (washing with EtOAc) The filtrate was concentrated in vacuo purified via MPLC eluting with 0-20% ethyl acetate in heptanes

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-Bromo-anisole (4.417 g, 23.6 mmol) was dissolved in acetonitrile (200 mL) and placed under an argon atmosphere in the absence of light. Iodobenzene diacetate (9.18 g, 28.5 mmol) was added followed by iodine (3.6 g, 14.2 mmol). The mixture was stirred for 16 hours at ambient temperature. The mixture was then poured into 1M Na2S2O3 (200 mL) and stirred until the solution was colourless. The solution was then extracted with diethyl ether (3×100 mL). The combined organic extracts were then washed with brine, dried with Na2SO4, filtered and evaporated to dryness. The crude product was filtered through a silica gel plug eluting with heptane/ethyl acetate (3:1) (200 mL). The filtrate was concentrated and the residue was distilled using a Kugelrohr apparatus collecting the compound at 75° C., 0.01 mbar. stirred until the solution The solution was then extracted with diethyl ether (3×100 mL) The combined organic extracts were then washed with brine dried with Na2SO4 filtered evaporated to dryness The crude product was filtered through a silica gel plug eluting with heptane/ethyl acetate (3:1) (200 mL) The filtrate was concentrated the residue was distilled collecting the compound at 75° C.