Thionyl Chloride → 3-Chloro-5-chloromethyl-2-ethyl-pyridine

HRID 900971Notes

Reaction equation

HRID 900971 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10]O)[CH:5]=[N:6][C:7]=1[CH2:8][CH3:9].S(Cl)([Cl:14])=O>>[Cl:1][C:2]1[C:7]([CH2:8][CH3:9])=[N:6][CH:5]=[C:4]([CH2:10][Cl:14])[CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 59698822(5-Chloro-6-ethyl-3-pyridinyl)methanol

Product 1

HCID 596988003-Chloro-5-chloromethyl-2-ethyl-pyridineYield 97.1%

Procedure

5-Chloro-6-ethyl-pyridin-3-yl-methanol (4.00 g, 23.3 mmol) is treated with thionyl chloride (50 mL, 685 mmol) and stirred at room temperature for 3 h. The excess SOCl2 is removed under reduced pressure. Water (300 mL) is added and the mixture is neutralized with solid Na2CO3. The precipitated product is filtered, washed with H2O (200 mL) and dried in vacuo to provide 3-chloro-5-chloromethyl-2-ethyl-pyridine as a light brown oil (4.3 g, 97%): Rf 0.54 (30% ethyl acetate in n-heptane), 1H NMR (CDCl3, 300 MHz) δ 8.42 (d, J=1.9 Hz 1 H), 7.70 (d, J=1.9 Hz, 1 H), 4.55 (s, 2 H), 2.97 (q, J=7.4 Hz, 2 H), 1.30 (t, J=7.4 Hz, 3 H). ESI-LCMS m/z calcd for C8H9Cl2N: 189.0; found 190.0 (M+1)+.

Workup

  1. customThe excess SOCl2 is removed under reduced pressure
  2. additionWater (300 mL) is added
  3. filtrationThe precipitated product is filtered
  4. washwashed with H2O (200 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-7bb24a735cb14bf788de443e4562fb55
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Reaction notes

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