Phosphorus tribromide → HCID 12941339, compound

HRID 2394094Notes

Reaction equation

HRID 2394094 reaction equation
P(Br)(Br)[Br:2].[C:5]1([CH2:11][CH2:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17]O)=[CH:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1(C)C=CC=CC=1>[C:5]1([CH2:11][CH2:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17][Br:2])=[CH:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 22293131HCID 22293131, compound

Product 1

HCID 12941339HCID 12941339, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3.14 ml (33.4 mmol) of phosphorus tribromide in 11 ml of toluene are added dropwise, while cooling and under an N2 atmosphere, to 8.36 g (85%; 33.4 mmol) of p-(2-phenylethyl)benzyl alcohol in 100 ml of toluene. After 2 h at RT, the mixture is poured onto ice-water and the organic phase is separated off; it is washed with sat. NaHCO3 solution, water and saline. The aqueous phases are extracted 2× with ether, and the combined organic phases are dried with Na2SO4 and evaporated: TLC Rf (A)=0.77; 1H-NMR (200 MHz, CDCl3): 2.92 (s, 4H), 4.50 (s, 2H), 7.15-7.35 (m, 9H); addition signals of approximately 20% p-(2-phenylethyl)toluene.

Workup

  1. additionthe mixture is poured onto ice-water
  2. customthe organic phase is separated off
  3. washit is washed with sat. NaHCO3 solution, water and saline
  4. extractionThe aqueous phases are extracted 2× with ether
  5. dry with materialthe combined organic phases are dried with Na2SO4
  6. customevaporated
  7. additionaddition signals of approximately 20% p-(2-phenylethyl)toluene

Sources & evidence

ORD record
ord-5aa50aa0e0604bd2b8d47f1b6d291771
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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