Phosphorus tribromide → HCID 18470429, compound

HRID 2228895Notes

Reaction equation

HRID 2228895 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]O)[CH:5]=[CH:6][C:7]=1[Cl:8].P(Br)(Br)[Br:19].C(=O)([O-])O.[Na+]>C(OCC)C>[Br:19][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]#[C:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 184701968-(3,4-Dichlorophenyl)oct-7-yn-1-ol

Product 1

HCID 18470429HCID 18470429, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 8-(3,4-dichlorophenyl)-oct-7-yn-1-ol (0.52 g) in diethyl ether (2.5 ml) was treated with phosphorous tribromide (0.23 g) at 0° C. (ice/salt bath). The solution was stirred at 0-5° C. for 2 h and allowed to warm to room temperature. Aqueous sodium hydrogen carbonate solution was added. The aqueous layer was extracted with further diethyl ether (2×5 ml) and the combined organic layers were washed with brine (5 ml) and dried over magnesium sulfate. Removal of the solvent under reduced pressure gave an oil that was chromatographed on silica gel using dichloromethane as eluent. This gave 8-bromo-1-(3,4-dichlorophenyl)-1-octyne (0.25 g). 1H-NMR (CDCl3) δ 1.35-1.7 (6H, m), 1.75-1.95 (2H, m), 2.33 (2H, t), 3.35 (2H, t), 7.13 (1H, dd), 7.27 (1H, d) and 7.40 (1H, d).

Workup

  1. temperatureto warm to room temperature
  2. extractionThe aqueous layer was extracted with further diethyl ether (2×5 ml)
  3. washthe combined organic layers were washed with brine (5 ml)
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent under reduced pressure
  6. customgave an oil that
  7. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-60664a844f6f4155bb718a7cb0c94048
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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