Bromide ion → (6-Phenylhexyl)phosphonic acid

HRID 1952426Notes

Reaction equation

HRID 1952426 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[P:14]([O:21]CC)([O:18]CC)[O:15]CC.[Br-]>>[C:8]1([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P:14](=[O:15])([OH:21])[OH:18])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 259Bromide ionHCID 31215Triethyl phosphiteHCID 561788(6-Bromohexyl)benzene

Product 1

HCID 20378153(6-Phenylhexyl)phosphonic acid

Procedure

The 1-bromo-6-phenylhexane (˜7.304 g, ˜30 mmol) from the previous step was then added to triethyl phosphite (25 mL, 143.7 mmol) in a round bottom flask fixed with a condenser and under Argon pressure. This was allowed to reflux overnight. GCMS (PJH-I-37b) showed no starting bromide left and the reaction was stopped. A distillation was performed to remove the excess triethyl phosphate and then a column in 2:1 hexane:ethyl acetate. The desired product had an Rf=0.55. The desired product was obtained with only a trace impurity of the bisphenyl substituted hexane. The product was be purified further as it is a new compound, but some of it was used in the next step.

Workup

  1. customfixed with a condenser and under Argon
  2. temperatureto reflux overnight
  3. waitleft
  4. distillationA distillation
  5. customto remove the excess triethyl phosphate

Sources & evidence

ORD record
ord-cc64b4a047c54856a1a36a1b68bf0c03
Source dataset
uspto-grants-2013_03
Patent number
US08405069B2

Reaction notes

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