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2,7-dibromonaphthalene

diethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalate

CsF

→

Tetraethyl 5,5′-(naphthalene-2,7-diyl)diisophthalate

수율 76.0%

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후처리

1. 1
   기타The flask was connected to a Schlenk
2. 2
   기타line and evacuated of air
3. 3
   workup.ADDITIONthen refilled with nitrogen
4. 4
   기타160 mL of 1,2-dimethoxyethane (DME) was degassed (two hours)
5. 5
   workup.ADDITIONadded to the flask through a canula
6. 6
   기타The flask was equipped with a water condenser
7. 7
   온도refluxed under nitrogen for 2 days
8. 8
   기타The solvent was removed on a rotary evaporator
9. 9
   workup.ADDITION120 mL of H2O was added
10. 10
    추출extracted with CHCl3
11. 11
    건조The organic phase was dried with MgSO4
12. 12
    기타After removal of the CHCl3 solvent
13. 13
    세척the crude product was washed with acetone
14. 14
    기타hexane (3×20 mL for each) to give a pure product with a yield of 76% (3.02 g)

실험 절차

To a 250 mL Schlenk flask, 2,7-dibromonaphthalene (2.00 g, 6.99 mmol), diethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalate (6.09 g, 17.48 mmol), CsF (4.00 g) and Pd(PPh3)4 (200 mg) were added. The flask was connected to a Schlenk line and evacuated of air then refilled with nitrogen. 160 mL of 1,2-dimethoxyethane (DME) was degassed (two hours) and added to the flask through a canula. The flask was equipped with a water condenser and refluxed under nitrogen for 2 days. The solvent was removed on a rotary evaporator. 120 mL of H2O was added and then extracted with CHCl3. The organic phase was dried with MgSO4. After removal of the CHCl3 solvent, the crude product was washed with acetone and then hexane (3×20 mL for each) to give a pure product with a yield of 76% (3.02 g) based on 2,7-dibromonaphthalene. 1H NMR (300 MHz, DMSO-d6): δ 1.39 (t, 12H), 4.42 (q, 8H), 7.90 (d, 2H), 8.11 (d, 2H), 8.45 (s, 4H), 8.52 (s, 4H).

출처