Phosphorus tribromide → HCID 58081170, compound

HRID 928444Notes

Reaction equation

HRID 928444 reaction equation
[CH3:1][C:2]1[C:11]([CH2:12]O)=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH3:15])=[CH:7][C:8]=2[CH3:14])[N:3]=1.P(Br)(Br)[Br:17]>C(Cl)Cl.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[Br:17][CH2:12][C:11]1[C:2]([CH3:1])=[N:3][C:4]2[C:9]([CH:10]=1)=[C:8]([CH3:14])[CH:7]=[C:6]([CH3:15])[CH:5]=2

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 58081283HCID 58081283, compound

Product 1

HCID 58081170HCID 58081170, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 86584982Sodium bicarbonate ethyl acetateSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (2,5,7-trimethylquinolin-3-yl)methanol (42.1 mg, 0.205 mmol) in DCM (1.5 ml) was added PBr3 (0.039 ml, 0.410 mmol). Reaction mixture was stirred overnight at 23° C. Reaction mixture was diluted with ethyl acetate/NaHCO3 sat. aq solution. Layers were separated and aqueous layer was extracted once more with ethyl acetate. Organic layer was dried over sodium sulfate, filtered and evaporated to afford the title compound. HPLC (Method G) Rt=1.409 min, MS (Method V) [M+H]+=264.2, 266.2.

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. customLayers were separated
  4. extractionaqueous layer was extracted once more with ethyl acetate
  5. dry with materialOrganic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6ec9d7601811479398bb7fc0be7f7a2d
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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