Phosphorus tribromide → HCID 67975802, compound

HRID 1053903Notes

Reaction equation

HRID 1053903 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12](=[O:18])[CH2:13][CH2:14][C:15]=2OC)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Br)(Br)[Br:20]>ClCCCl>[Br:20][C:15]1[CH2:14][CH2:13][C:12](=[O:18])[C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 67975877HCID 67975877, compound

Product 1

HCID 67975802HCID 67975802, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of Example 7C (245 mg, 1.003 mmol) in 1,2-dichloroethane (5 mL) was added PBr3 (0.142 mL, 1.504 mmol). The resulting mixture was heated to reflux for 1 hour, then cooled to ambient temperature, and poured over cracked ice. The organic layer was separated, washed with saturated aqueous NaHCO3 (5 mL), and dried over MgSO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (on silica gel, eluted with dichloromethane/methanol=200:1, v/v) to afford the title compound (200 mg, 0.682 mmol, 68.0% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.38 (s, 4H), 3.00-3.03 (m, 2H), 2.62-2.65 (m, 2H), 1.26 (s, 9H); LC/MS (ESI) m/z 293 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1 hour
  3. additionpoured over cracked ice
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaHCO3 (5 mL)
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography (on silica gel
  9. washeluted with dichloromethane/methanol=200:1

Sources & evidence

ORD record
ord-94b2c9567be14cbe9ddcb87d14bf593f
Source dataset
uspto-grants-2016_07
Patent number
US09394279B2

Reaction notes

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