Carbon tetrabromide → 2-Bromo-6-(1-bromo-2-fluoroethyl)pyridine

HRID 385997Notes

Reaction equation

HRID 385997 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8](O)[CH2:9][F:10])[CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:8]([Br:32])[CH2:9][F:10])[N:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 595259001-(6-Bromopyridin-2-yl)-2-fluoroethanol

Product 1

HCID 595262542-Bromo-6-(1-bromo-2-fluoroethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(6-Bromopyridin-2-yl)-2-fluoroethanol (0.525 g, 2.39 mmol) and triphenylphosphine (1.252 g, 4.77 mmol) were taken up in DCM (25 mL). A solution of carbon tetrabromide (1.582 g, 4.77 mmol) in DCM (10 mL) was added and the resulting mixture stirred at room temperature overnight. The precipitate was removed by filtration and the filtrate concentrated in vacuo. Purification of the residue by silica gel column chromatography (0-10% EtOAc-hexanes) gave the title compound as a colorless oil.

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification of the residue by silica gel column chromatography (0-10% EtOAc-hexanes)

Sources & evidence

ORD record
ord-3690968ecc6f47458254116afc17fff1
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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