Thionyl Chloride → 4-Bromo-2-(chloromethyl)pyridine

HRID 1446076

Reaction equation

HRID 1446076 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]O)[CH:3]=1.O=S(Cl)[Cl:12].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][Cl:12])[CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 14761462(4-Bromopyridin-2-yl)methanol

Product 1

HCID 533020224-Bromo-2-(chloromethyl)pyridineYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-pyridylmethanol (3.38 g, 0.016 mol) in CH2Cl2 (210 mL) was slowly added SOCl2 (21 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 20 h, then satd. NaHCO3 was added. The organic layer was washed with brine, dried (MgSO4), and concentrated to give crude 4-bromo-2-(chloromethyl)pyridine (2.93 g, 79%) as a yellow oil. APCI MS m/z 205.7, 207.7 (M+H). 1H NMR (400 MHz, (CD3)2SO) δ 8.47 (d, J=5.3 Hz, 1H), 7.68 (d, J=1.7 Hz, 1H), 7.42 (dd, J=5.3, 1.75 Hz, 1H), 4.64 (s, 2H).

Workup

  1. customat 0° C
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-807c2fcf1329462484fec43fb31911f1
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Linked notes

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