Thionyl bromide → 5-(Bromomethyl)-2-methylpyridine--hydrogen bromide (1/1)

HRID 1825328Notes

Reaction equation

HRID 1825328 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.S(Br)([Br:12])=O>ClCCl>[BrH:12].[Br:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 68176Thionyl bromideHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 221456055-(Bromomethyl)-2-methylpyridine--hydrogen bromide (1/1)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (6-methylpyridin-3-yl)methanol (J. Med. Chem. 43; 18; 2000; 3386) (492 mg, 4 mmol) and thionyl bromide (4.16 g, 20 mmol) in dichloromethane (20 ml) was stirred at room temperature for 3 hours. The reaction was concentrated under reduced pressure and the residue azeotroped with dichloromethane. The residual red oil was triturated well with ether to afford the title compound as an orange powder, 1.39 g; 1H NMR (DMSOd6, 400 MHz) δ: 2.64 (s, 3H), 4.81 (s, 2H), 7.81 (d, 1H), 8.42 (d, 1H), 8.84 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue azeotroped with dichloromethane
  3. customThe residual red oil was triturated well with ether

Sources & evidence

ORD record
ord-e3848b514e54498a87eb558e8dcdaa0e
Source dataset
uspto-grants-2006_05
Patent number
US07045653B2

Reaction notes

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