Phosphorus oxybromide → HCID 53429144, compound

HRID 595180Notes

Reaction equation

HRID 595180 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)([Br:19])=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][Br:19])=[CH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24613Phosphorus oxybromideHCID 59255139(6-(Benzyloxy)pyridin-3-yl)methanol

Product 1

HCID 53429144HCID 53429144, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
20 °C

Procedure

(6-(Benzyloxy)pyridin-3-yl)methanol (3 g, 14 mmol) was added to a solution of phosphorus oxybromide (4.8 g, 16.8 mmol) in DCM (40 mL) under N2 at 0° C. The mixture was stirred at 20° C. for 1 hour. The mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc) to afford 2-(benzyloxy)-5-(bromomethyl)pyridine. MS ESI calc'd. for C13H13BrNO [M+H]+ 278 and 280. found 278 and 280. 1H NMR (400 MHz, DMSO-d6) δ 8.27 (d, J=2.4 Hz, 1H), 7.81-7.79 (m, 1H), 7.45-7.31 (m, 5H), 6.90 (d, J=8.4 Hz, 1H), 5.35 (s, 2H), 4.72 (s, 2H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-d43117a1d826455fbcb3ea81953ae8a1
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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