Water → HCID 67078811, compound

HRID 84992Notes

Reaction equation

HRID 84992 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][P:24](=[O:31])([O:28]CC)[O:25]CC.Br[Si](C)(C)C.O>ClCCl.CO>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][P:24](=[O:25])([OH:31])[OH:28]

Participants

6

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 86653412Diethyl 12-(1,3-dioxoisoindolin-2-yl)dodecylphosphonate

Product 1

HCID 67078811HCID 67078811, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Diethyl 12-(1,3-dioxoisoindolin-2-yl)dodecylphosphonate (2.00 g, 4.43 mmol) was dissolved in dry dichloromethane (25 mL). Bromotrimethylsilane (1.8 mL, 14.2 mmol) was added via syringe. The reaction was capped with a greased glass stopper and allowed to stir overnight. The volatiles were removed under reduced pressure to yield a yellow oil. This was dissolved in 10:1 methanol:water (20 mL) and allowed to stir overnight. After removing the solvents, recrystallization in acetonitrile yielded a white powdery solid (1.709 g, 98% yield). 1H NMR (400.14 MHz, DMSO) δ 7.84 (m, 4H), 3.54 (t, J=7.1 Hz, 2H), 1.58-1.53 (m, 2H), 1.50-1.31 (m, 4H), 1.30-1.20 (m, 16H). 13C {1H} NMR (100.62 MHz, DMSO) δ 167.9 (2C), 134.4 (2C), 131.6 (2C), 123.0 (2C), 37.36, 30.08 (d, J=15.8 Hz), 28.99, 28.95, 28.87 (2C), 28.70, 28.53, 27.85, 27.54 (d, J=136.5 Hz), 26.22, 22.73, (d, J=4.58 Hz). 31P {1H} NMR (161.97 MHz, DMSO): δ 27.74. MS (FAB, m/z): 396.2 (M+, 100%). Exact mass calculated (found) for [M+H]+, m/z): 396.19399 (396.19445). Analysis calculated (found) %: C 60.75 (60.64), H 7.65 (7.80).

Workup

  1. customThe reaction was capped with a greased glass stopper
  2. customThe volatiles were removed under reduced pressure
  3. customto yield a yellow oil
  4. stirringto stir overnight
  5. customAfter removing
  6. customthe solvents, recrystallization in acetonitrile

Sources & evidence

ORD record
ord-c696d6551d1b48a78f1b9d4d53b28beb
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Reaction notes

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