Methanol → {[(9H-Carbazol-2-yl)oxy]methyl}phosphonic acid

HRID 1866481Notes

Reaction equation

HRID 1866481 reaction equation
C([O:3][P:4]([CH2:9][O:10][C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH:12]=1)(=[O:8])[O:5]CC)C.C[Si](I)(C)C.CO>ClCCl>[CH:12]1[C:13]2[NH:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]=2[CH:22]=[CH:23][C:11]=1[O:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 71402677Diethyl {[(9H-carbazol-2-yl)oxy]methyl}phosphonate

Product 1

HCID 68480495{[(9H-Carbazol-2-yl)oxy]methyl}phosphonic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of diethyl-2-carbazolyloxymethylphosphonate (0.33 g, 1 mmol) dissolved in dry dichloromethane (8 ml) under an atmosphere of nitrogen was added trimethyl silyl iodide (0.6 ml). The red solution was stirred for 2 h then methanol (15 ml) was added. After 2 h the solvent was removed under reduced pressure and then water (20 ml) was added to the residue. The mixture was concentrated under reduced pressure. Water (20 ml) was added and the mixture was concentrated under reduced pressure. This was repeated four times to afford 2-carbazolyloxymethyl phosphonic acid as a yellow green solid (0.26 g, 95%), m.p. 291° C., High Resolution Mass Spec. Pound: 277.0496, C13H12NO4PM+ requires 277.0504. δH (270 MHz, DMSO-d6) 11.13 (1H, s), 7.983 (1H, d, J 5.7 Hz), 7.98 (1H, d, J 5.7 Hz), 7.42 (1H, d, J 8 Hz), 7.28 (1H, dd, J1 8 Hz, J2 8 Hz), 7.10 (1H, dd, J1 8 Hz, J2 8 Hz), 7.05 (1H, d, J 2 Hz), 6.81 (1H, dd, J1 8 Hz, J2 2 Hz), 4.17 (2H, d, J 10.2 Hz), λex (DMSO, nm) 385, λem 421.

Workup

  1. customAfter 2 h the solvent was removed under reduced pressure
  2. additionwater (20 ml) was added to the residue
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionWater (20 ml) was added
  5. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6c30fda9abf74d1286afc35272cd673a
Source dataset
uspto-grants-2009_12
Patent number
US07629379B2

Reaction notes

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