Ethanol → HCID 15786023, compound

HRID 1492905Notes

Reaction equation

HRID 1492905 reaction equation
[Br:1][C:2](Br)([P:19](=[O:34])([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[P:3](=[O:18])([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(O)C.Cl[Sn]Cl>O>[Br:1][CH:2]([P:3](=[O:18])([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[P:19](=[O:34])([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 702EthanolHCID 24479Stannous ChlorideHCID 14957296HCID 14957296, compound

Product 1

HCID 15786023HCID 15786023, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Into a solution containing 6.7 g (0.01 moles) of tetrahexyl (dibromomethylene)bisphosphonate in 70 ml of abs. ethanol, 2.5 g of SnCl2 ×2H2O in 100 ml of water are added while stirring at 0° C. After the addition, the mixture is stirred for 15 minutes and extracted with chloroform and the extract is dried (MgSO4) and filtered. The filtrate is evaporated under a vacuum, whereby about 4.1 g (70% of the theor.) of tetrahexyl (monobromomethylene)bisphosponate (31P-NMR (CDCl3): δ 13.83 ppm) are obtained as a colourless oil, at a concentration of 90%.

Workup

  1. additionAfter the addition
  2. stirringthe mixture is stirred for 15 minutes
  3. extractionextracted with chloroform
  4. dry with materialthe extract is dried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate is evaporated under a vacuum, whereby about 4.1 g (70% of the theor

Sources & evidence

ORD record
ord-fdfd4b3c8f7944358f16046455f20195
Source dataset
uspto-grants-1994_12
Patent number
US05376649

Reaction notes

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