Carbon tetrabromide → 2-(1-Bromopropyl)-6-chloropyridine

HRID 1048488Notes

Reaction equation

HRID 1048488 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8](O)[CH2:9][CH3:10])[CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:13][CH:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 585740021-(6-Chloropyridin-2-yl)propan-1-ol

Product 1

HCID 585733532-(1-Bromopropyl)-6-chloropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(6-chloropyridin-2-yl)propan-1-ol (0.497 g, 2.90 mmol), CBr4 (1.2 g, 3.62 mmol) and triphenylphosphine (0.987 g, 3.76 mmol) in 25 mL of THF was stirred at room temperature for 2 h. The solid was filtered off and washed with THF. The filtrate was concentrated and residue was purified by chromatography on silica gel, eluting with 10 to 50% EtOAc/hexane to provide the title compound. Mass Spectrum (ESI) m/z=236 (M+1).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated
  4. customresidue was purified by chromatography on silica gel
  5. washeluting with 10 to 50% EtOAc/hexane

Sources & evidence

ORD record
ord-b8247dbb772f4e389f7d85c2448ce531
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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