Thionyl Chloride → 2-Bromo-6-(chloromethyl)pyridine--hydrogen chloride (1/1)

HRID 1620154Notes

Reaction equation

HRID 1620154 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]O)[N:3]=1.O=S(Cl)[Cl:12]>C(Cl)Cl>[ClH:12].[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Cl:12])[N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3517811(6-Bromopyridin-2-yl)methanol

Product 1

HCID 534166742-Bromo-6-(chloromethyl)pyridine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-6-(hydroxymethyl)pyridine (0.54 g, 2.87 mmol) in dry CH2Cl2 (10 mL) at 0° C. under N2 in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise SOCl2 (4.2 mL, 57.90 mmol) and the mixture was stirred for 2 h at RT. The volatiles were then removed at 40° C. under vacuum and the residue was taken up in CHCl3 (20 mL) before concentration back to dryness at 40° C. under vacuum (done twice) to give 2-bromo-6-(chloromethyl)pyridine hydrochloride CCH 34150-1 as a brown solid (0.65 g, 93% yield).

Workup

  1. customThe volatiles were then removed at 40° C. under vacuum
  2. concentrationthe residue was taken up in CHCl3 (20 mL) before concentration back to dryness at 40° C. under vacuum (

Sources & evidence

ORD record
ord-b7cb9f873fbc4a718c3768b026fc498b
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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