Carbon tetrabromide → 3-(2-bromoethyl)pyridine

HRID 1819412Notes

Reaction equation

HRID 1819412 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8]O)[CH:2]=1.C(Br)(Br)(Br)[Br:11].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Br:11][CH2:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 805153-Pyridineethanol

Product 1

HCID 111167423-(2-bromoethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(3-pyridyl)ethan-1-ol (100 mg, 0.79 mmol) and CBr4 (314 mg, 0.95 mmol) in THF (2 mL) was cooled to 0° C. and PPh3 (313 mg, 1.18 mmol) was added portionwise. The ice-bath was removed and the reaction mixture was stirred at room temperature for 16 h. The mixture was concentrated and diluted with CH2Cl2. The mixture was basified using saturated NaHCO3 and the organic phase was separated. The aqueous phase was re-extracted with CH2Cl2 and the combined organic phase was dried over Na2SO4 and concentrated. Silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluent afforded 3-(2-bromo-ethyl)-pyridine.

Workup

  1. customThe ice-bath was removed
  2. concentrationThe mixture was concentrated
  3. additiondiluted with CH2Cl2
  4. customthe organic phase was separated
  5. extractionThe aqueous phase was re-extracted with CH2Cl2
  6. dry with materialthe combined organic phase was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2415d907df544637a9117833e080e320
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

Loading…