HCID 12753707, compound → [3-(9H-Carbazol-9-YL)propyl]phosphonic acid

HRID 1952423Notes

Reaction equation

HRID 1952423 reaction equation
C[Si](C[Si](Br)(C)C)(C)C.[CH:10]1[C:22]2[N:21]([CH2:23][CH2:24][CH2:25][P:26](=[O:33])([O:30]CC)[O:27]CC)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[CH:10]1[C:22]2[N:21]([CH2:23][CH2:24][CH2:25][P:26](=[O:27])([OH:30])[OH:33])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 12753707HCID 12753707, compoundHCID 59172007HCID 59172007, compound

Product 1

HCID 59172009[3-(9H-Carbazol-9-YL)propyl]phosphonic acidYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl(TMS)-bromide (1.12 mL, 8.67 mmol) was added via syringe to a solution of diethyl 3-(9H-carbazol-9-yl)propylphosphonate (1.00 g, 2.89 mmol) in ˜20 mL dry DCM in a 50 mL rbf. The flask was greased and capped and allowed to stir for 90 minutes. The volatile organics were removed under vacuum and 30 mL of 1:1 MeOH:H2O were added. The solution turned a cloudy whitish/grey. The solvents were removed and the product recrystallized from 2:1 H2O:acetone (grey powder, 612 mg) and 1:1 H2O:MeOH (PJH-II-5c, glassy grey solid, 42 mg). Both recrystallization solvents yielded pure product. Total yield was 78%. 1H NMR (400.14 MHz, DMSO) δ 8.15 (d, J=8.00 Hz, 2H), 7.65 (d, J=8.00 Hz, 2H), 7.45 (dt, J=15.41, 1.00 Hz, 2H), 7.19 (t, J=14.81 Hz, 2H), 4.48 (t, J=13.60 Hz, 2H), 2.03-1.89 (m, 2H), 1.59-1.46 (m, 2H). 13C{1H} NMR (100.62 MHz, DMSO) δ 140.01 (2C), 125.76 (2C), 122.07 (2C), 120.33 (2C), 118.78 (2C), 108.33 (2C), 42.48 (d, J=17.31 Hz), 25.00 (d, J=137.35 Hz), 22.67 (d, J=4.13 Hz). 31P{1H} NMR (161.97 MHz, DMSO): δ 26.78. Analysis found (calculated) %: C, 62.27 (62.28); H, 5.56 (5.58); N, 4.73 (4.84). MS (FAB, m/z): 290 ([M+H]+, 100%). Exact mass found (calculated for [M+H]+, m/z): 290.09405 (290.09461).

Workup

  1. customcapped
  2. customThe volatile organics were removed under vacuum and 30 mL of 1:1 MeOH
  3. additionH2O were added
  4. customThe solvents were removed
  5. customthe product recrystallized from 2:1 H2O
  6. customBoth recrystallization solvents yielded pure product

Sources & evidence

ORD record
ord-cbb23c352a584a9dbfbba77abbd8f320
Source dataset
uspto-grants-2013_03
Patent number
US08405069B2

Reaction notes

Loading…