Thionyl Chloride → 5-bromo-2-(chloromethyl)pyridine

HRID 1487469Notes

Reaction equation

HRID 1487469 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][Cl:12])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 114015015-bromo-2-(chloromethyl)pyridineYield 72.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of (5-Bromo-pyridin-2-yl)-methanol (1 g, 5.319 mmol) in CH2Cl2 (20 mL) is added drop wise thionyl chloride (0.57 mL, 7.979 mmol) at 0° C. then stirred for another 4 hours. Reaction mixture is diluted with saturated sodium bicarbonate solution and extracted with CH2Cl2. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography using 7% ethyl acetate in hexane as an eluent to afford the title compound (0.8 g). 1HNMR (400 MHz, DMSO-d6) δ: 4.7 (s, 2H), 7.53 (d, 8.36 Hz, 1H), 8.09-8.11 (dd, J1=2.44 Hz, J2=8.23 Hz, 1H), 8.69 (d, J=2.4 Hz, 1H), LC-MS (M/Z): [M+H]=206.0.

Workup

  1. customReaction mixture
  2. extractionextracted with CH2Cl2
  3. dry with materialOrganic layer is dried over sodium sulphate, solvent
  4. customis evaporated in vacuo
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-60b1bca172bf41bb832e4b2326491fdb
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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