Phosphorus tribromide → 1372891-51-4

HRID 1625066Notes

Reaction equation

HRID 1625066 reaction equation
[F:1][C:2]1[C:3]([CH2:9]O)=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].P(Br)(Br)[Br:12]>C1COCC1>[Br:12][CH2:9][C:3]1[C:2]([F:1])=[C:7]([CH3:8])[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 68277844HCID 68277844, compound

Product 1

HCID 866916061372891-51-4Yield 104.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 6 ((3-fluoro-4-methyl-2-pyridinyl)methanol, 246 mg, 1.743 mmol) was dissolved in 10 mL of anhydrous THF. Phosphorous tribromide (ALDRICH, 519 mg, 1.917 mmol) was added. Reaction mixture was stirred at room temperature overnight. Solvent was evaporated and residue was partitioned between Et2O and NaHCO3 (aqueous saturated solution). Organic layer was dried over MgSO4 (anh), filtered and concentrated to give the title compound (372 mg, quantitative yield). 1H NMR (300 MHz, DMSO-d6) δ ppm: 8.23-8.24 (m, 1H), 7.34-7.37 (m, 1H), 4.66 (s, 2H), 2.28 (s, 3H). [ES+MS] m/z 204 (M).

Workup

  1. customReaction mixture
  2. customSolvent was evaporated
  3. customresidue was partitioned between Et2O and NaHCO3 (aqueous saturated solution)
  4. dry with materialOrganic layer was dried over MgSO4 (anh)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-00520d7642d740b1abd77cf5b68907aa
Source dataset
uspto-grants-2014_07
Patent number
US08779153B2

Reaction notes

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