Triphenylphosphine → 2-(1-Bromoethyl)pyridine

HRID 2041314Notes

Reaction equation

HRID 2041314 reaction equation
O[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:36])C(=O)C1>C(Cl)Cl>[Br:36][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 86784alpha-Methyl-2-pyridinemethanol

Product 1

HCID 153736572-(1-Bromoethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (±)-2-(1-hydroxyethyl)-pyridine (Bull. Chem. Soc. Jpn. 1990, 63, 461-465) (10.0 g, 81.3 mmol) in DCM (120 mL) at 0° C., add with stirring triphenylphosphine (22.39 g, 85.365 mmol) followed by NBS (15.2 g, 85.4 mmol) in portions. Warm the reaction mixture to ambient temperature and continue stirring for 3 h. Concentrate in vacuo and purify by chromatography on silica gel eluting with hexane/EtOAc (19:1) to give the title compound.

Workup

  1. concentrationConcentrate in vacuo
  2. custompurify by chromatography on silica gel eluting with hexane/EtOAc (19:1)

Sources & evidence

ORD record
ord-32ad17aab11d4712bcd3498175b3e13b
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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