Thionyl Chloride → 3-Bromo-5-(chloromethyl)pyridine

HRID 433607

Reaction equation

HRID 433607 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:7]=[C:8]([CH2:12]O)[CH:9]=[N:10][CH:11]=1>CCOCC>[Br:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]([CH2:12][Cl:3])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 117012593-Bromo-5-(chloromethyl)pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
4 °C

Procedure

To a cooled solution of thionylchloride (41 ml, 344 mmol) at 0° C. was added cautiously (highly exothermic) portionwise (5-bromo-pyridin-3-yl)-methanol (10 g, 44.5 mmol). After complete addition the mixture was heated to reflux for 1 h to complete the reaction. After cooling, ether (50 ml) was added and the mixture cooled to 4° C. The precipitated solid was filtered off and washed with cold ether then dried at 50° C. under vacuum for 2 h to afford the title compound (9.1 g, 84%) as a light yellow solid. MS: m/e=206.9 (M+).

Workup

  1. additionAfter complete addition the mixture
  2. temperaturewas heated
  3. temperatureto reflux for 1 h
  4. customthe reaction
  5. temperatureAfter cooling
  6. filtrationThe precipitated solid was filtered off
  7. washwashed with cold ether
  8. customthen dried at 50° C. under vacuum for 2 h

Sources & evidence

ORD record
ord-e8c1a2c5785749f182fbf880b869b40b
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Linked notes

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