Water → HCID 86682206, compound

HRID 518940Notes

Reaction equation

HRID 518940 reaction equation
[OH-:1].[Na+].[I:3][C:4]1[C:11]([I:12])=[CH:10][C:9]([I:13])=[CH:8][C:5]=1[CH2:6]Br.O>CN1C(=O)CCC1>[I:3][C:4]1[C:11]([I:12])=[CH:10][C:9]([I:13])=[CH:8][C:5]=1[CH2:6][O:1][CH2:6][C:5]1[CH:8]=[C:9]([I:13])[CH:10]=[C:11]([I:12])[C:4]=1[I:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 534030771-(Bromomethyl)-2,3,5-triiodobenzene

Product 1

HCID 86682206HCID 86682206, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

447 mg of PVA 13 kDa (9 mmol, 1 eq) was dissolved in 30 ml of dry NMP (concentration of PVA: 0.3M) under nitrogen gas flow. The reaction mixture was stirred for 5 minutes at 130° C.; then the temperature was decreased to 50° C. 727 mg of ground and dried NaOH (18 mmol, 2 eq) was added and the mixture was stirred for 10 minutes. Then, 5 g of 2,3,5-triiodobenzyl bromide (9 mmol, 1 eq) was added. After 30 minutes, the mixture was cooled to room temperature and 30 ml of cold water was added under stirring. A solid precipitate appeared, was filtered and washed with methanol. After conventional steps of purification, 800 mg of TIB-PVA 13 kDa including 26% of residual NMP was obtained (representing 208 mg of NMP and 592 mg of TIB-PVA 13 kDa).

Workup

  1. customwas decreased to 50° C
  2. stirringthe mixture was stirred for 10 minutes
  3. waitAfter 30 minutes
  4. temperaturethe mixture was cooled to room temperature
  5. stirringunder stirring
  6. filtrationwas filtered
  7. washwashed with methanol
  8. customAfter conventional steps of purification, 800 mg of TIB-PVA 13 kDa
  9. customwas obtained (representing 208 mg of NMP and 592 mg of TIB-PVA 13 kDa)

Sources & evidence

ORD record
ord-2d1b2b17d39a48be9447783de311c0a9
Source dataset
uspto-grants-2015_08
Patent number
US09115230B2

Reaction notes

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