Benzyl Alcohol → 6-(Benzyloxy)-2-bromo-3-chloropyridine

HRID 1521943Notes

Reaction equation

HRID 1521943 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[Br:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[C:18](F)[N:17]=1>O1CCCC1.C(OCC)(=O)C.O>[CH2:1]([O:8][C:18]1[N:17]=[C:16]([Br:15])[C:21]([Cl:22])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 23665647Potassium tert-butoxideHCID 754123402-Bromo-3-chloro-6-fluoropyridine

Product 1

HCID 904122516-(Benzyloxy)-2-bromo-3-chloropyridine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl alcohol (55.5 mg, 0.513 mmol) in tetrahydrofuran (5 mL) at 0° C. was added potassium tert-butoxide (57.6 mg, 0.513 mmol) and the mixture was stirred at 0° C. for 2 hours. The mixture was cooled to −78° C. and a solution of 2-bromo-3-chloro-6-fluoropyridine (120 mg, 0.570 mmol) in 2 mL tetrahydrofuran was added. After stirring at −78° C. for 1 hour the mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over sodium sulfate and concentrated. Purification by column chromatography (silica gel, 20% ethyl acetate in hexane) afforded the title compound. LCMS: 299.9 (M+3)+.

Workup

  1. temperatureThe mixture was cooled to −78° C.
  2. stirringAfter stirring at −78° C. for 1 hour the mixture
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by column chromatography (silica gel, 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9c22a9f1bb3846c297b3deb79a3df96e
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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