Compound 2'
2,7-diiodophenanthrene
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Method 1: A mixture of compound 1’ (1.08 g, 2.50 mmol) and DDQ (3.40 g, 15.0 mmol) in dry benzene was heated under reflux for 3 days. Then benzene was removed under vacuum. The crude was purified by flash chromatography (DCM/Hexane 1:4) to give compound 2’ as pale yellow solid (1.06 g, 98%).
Method 2: Compound 1’ (6.91 g, 16.0 mmol), NBS (3.13 g, 17.6 mmol) and BPO (194 mg, 0.80 mmol) were added to CCl4 (400 mL). The resulting mixture was refluxed for 5 hours. Then cooled to room temperature, acetic acid (48 mL) and potassium acetate (47.1 g, 0.48 mol) were added. The reaction mixture was refluxed for another 15 hours. After cooling to room temperature, Na2SO3 was added and stirred for 0.5 hour. The mixture was extracted by dichloromethane (400 mL), washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude was purified by flash chromatography (DCM/Hexane 1:2) to give compound 2’ as pale yellow solid (6.81 g, 99%). Data for 2’: 1H NMR (500 MHz, CDCl3): δ 7.62 (s, 2H), 7.91 (dd, J1 = 1.8 Hz, J2 = 8.8 Hz, 2H), 8.25 (d, J = 1.5 Hz, 2H), 8.33 (d, J = 8.5 Hz, 2H).
- PubChemID:
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350082700
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