Benzyl Alcohol → 3-(Benzyloxy)-5-bromopyridine

HRID 244583

Reaction equation

HRID 244583 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.[CH2:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:9]([O:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 153891983-(Benzyloxy)-5-bromopyridineYield 31.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a vial is added 3-bromo-5-hydroxypyridine (200 mg, 1.15 mmol), benzyl alcohol (137 mg, 1.27 mmol) and triphenylphosphine (332 mg, 1.27 mmol) in THF (5 ml) at 0° C., followed by the addition of diisopropyl azodicarboxylate (256 mg, 1.27 mmol). The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is concentrated in vacuo. The residue is diluted with EtOAc, washed with sat NaHCO3, water, brine, dried under anhy. Na2SO4, filtered and concentrated. The residue is purified by flash chromatography (SiO2, 0-5% MeOH/CH2Cl2) to afford title compound (97 mg); m/z 264.0, 266.0 [M, M+2H]

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionThe residue is diluted with EtOAc
  3. washwashed
  4. customdried under anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography (SiO2, 0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-dee370fb0bb64f7abb21b48bbf5c10cd
Source dataset
uspto-grants-2014_02
Patent number
US08658661B2

Linked notes

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