Water → HCID 131728703, compound

HRID 1365482Notes

Reaction equation

HRID 1365482 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[CH2:22]([C:25](O)(O)[C:26]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH3:27])[CH2:23][CH3:24].O>C(#N)C>[Br-:20].[Br-:20].[CH2:22]([CH2:25][C:26]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)([CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1)[CH3:27])[CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 24408BromineHCID 23066954HCID 23066954, compound

Product 1

HCID 131728703HCID 131728703, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

Triphenylphosphine (0.4 mol) is suspended in acetonitrile and cooled to 10° C., and bromine (0.39 mol) is added at this temperature. The suspension is stirred for a further 1 hour, and propyldicyclohexylpropane-diol B3.7 (0.2 mol) is then added. The mixture is stirred overnight at room temperature and subsequently refluxed for 4 hours. After cooling to room temperature, water is added, and the mixture is extracted with petroleum ether. The organic phase is dried and evaporated, and the residue is filtered through silica gel. Evaporation gives propyldicyclohexylpropane dibromide B3.8. Yield: 94%.

Workup

  1. addition(0.2 mol) is then added
  2. stirringThe mixture is stirred overnight at room temperature
  3. temperaturesubsequently refluxed for 4 hours
  4. temperatureAfter cooling to room temperature
  5. extractionthe mixture is extracted with petroleum ether
  6. customThe organic phase is dried
  7. customevaporated
  8. filtrationthe residue is filtered through silica gel
  9. customEvaporation

Sources & evidence

ORD record
ord-4445d0b885b64e3c891b7b6cef1437a6
Source dataset
uspto-grants-2011_02
Patent number
US07888519B2

Reaction notes

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