1,2-Dibromoethane → 2-Bromo-ethyl-phenanthridinium bromide

HRID 550855Notes

Reaction equation

HRID 550855 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[Br:15][CH2:16][CH2:17]Br.[K+].[Br-]>>[Br-:15].[Br:15][CH2:16][CH2:17][C:1]1[C:14]2[C:5](=[NH+:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 78391,2-DibromoethaneHCID 9189PhenanthridineHCID 253877Potassium Bromide

Product 1

HCID 671881532-Bromo-ethyl-phenanthridinium bromideYield 95%

Conditions

Temperature
110 °C

Procedure

Phenanthridine (5.44 g; 30.4 mmol) was dissolved in 1,2-Dibromoethane (114.2 g; 52 ml; 608 mmol) and stirred at 110° C. for three days. During that time, a white precipitate was formed and was filtered off every 12 hours. After each filtration, the precipitate was rinsed with an additional 5 ml of 1,2-Dibromoethane and the mother liquor was stirred at 90° C. until the next filtration. The reaction was complete after ca. three days when no more precipitate formed. The filtrates were combined and washed thoroughly with ether and with ethyl acetate to give 2 (7.92 g; 21.6 mmol) as a beige powder in a 95% yield; mp: 234-235° C. (dec.); 1H NMR (D2O, 400 MHz): δ 9.81 (s, 1H), 8.72 (d, 1H, J=7.2 Hz), 8.63 (d, 1H, J=7.2 Hz), 8.37 (d, 1H, J=7.2 Hz), 8.26 (d, 1H, J=7.2 Hz), 8.18 (t, 1H, J=7.2 Hz), 7.98 (t, 1H, J=7.2 Hz), 7.90 (m, 2H), 5.37 (t, 2H, J=5.8 Hz), 4.05 (t, 2H, J=5.8 Hz); 13C NMR (D2O, 100 MHz): δ 155.27 (CH), 139.03 (CH), 135.59 (C), 133.18 (CH), 132.78 (C), 132.58 (CH), 130.85 (CH), 130.72 (CH), 126.57 (C), 125.13 (CH), 123.32 (C), 123.00 (CH), 118.91 (CH), 58.87 (CH2), 29.41 (CH2); IR (KBr, cm−1): 2947(w), 1620(m), 763(s), 717(m); MS (ES): 288.1 (M−Br) (100), 206.2 (8); Anal. Calcd for C15H13NBr2: C, 49.32; H, 3.59; N, 3.84. Found: C, 49.15; H, 3.48; N, 3.76.

Workup

  1. customDuring that time, a white precipitate was formed
  2. filtrationwas filtered off every 12 hours
  3. filtrationAfter each filtration
  4. washthe precipitate was rinsed with an additional 5 ml of 1,2-Dibromoethane
  5. stirringthe mother liquor was stirred at 90° C. until the next filtration
  6. waitThe reaction was complete after ca. three days
  7. customwhen no more precipitate formed
  8. washwashed thoroughly with ether and with ethyl acetate
  9. customto give 2 (7.92 g; 21.6 mmol) as a beige powder in a 95% yield

Sources & evidence

ORD record
ord-d562d4be533e4584a3e3f425c0e6aa44
Source dataset
uspto-grants-2011_05
Patent number
US07947703B2

Reaction notes

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