Phosphorus tribromide → HCID 22292450, compound

HRID 966865Notes

Reaction equation

HRID 966865 reaction equation
O[CH2:2][C:3]1[S:4][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:6][CH:7]=1.P(Br)(Br)[Br:14]>C(OCC)C>[Br:14][CH2:2][C:3]1[S:4][C:5]([S:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 22292447[5-(Butylsulfanyl)thiophen-2-yl]methanol

Product 1

HCID 22292450HCID 22292450, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of crude 46 (55.4 g, 0.274 mol) in anhydrous ethyl ether (70 mL) was added dropwise to a solution of phosphorus tribromide (12.9 mL, 0.137 mol) in anhydrous ethyl ether (300 mL) at 0° C. After addition was complete, the mixture was allowed to warm slowly to room temperature and stirred for 4 hours under nitrogen. The mixture was then extracted with ethyl ether (3×150 mL). The combined organic solution was washed with brine and dried (MgSO4). MgSO4 was removed by filtration and the crude product was carried to the next step without the removal of solvent to prevent product decomposition.

Workup

  1. additionAfter addition
  2. extractionThe mixture was then extracted with ethyl ether (3×150 mL)
  3. washThe combined organic solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. customMgSO4 was removed by filtration
  6. customthe crude product was carried to the next step without the removal of solvent

Sources & evidence

ORD record
ord-1a2e3500206c4e9e9bc656b32f0e29d9
Source dataset
uspto-grants-2005_10
Patent number
US06953570B2

Reaction notes

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