Thionyl Chloride → HCID 86094445, compound

HRID 2099567Notes

Reaction equation

HRID 2099567 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[N:11]=2)O)[CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:20]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:8]([Cl:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[N:11]=2)[N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86602989HCID 86602989, compound

Product 1

HCID 86094445HCID 86094445, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (6-bromopyridin-2-yl)(6-methoxypyridin-2-yl)methanol (5.11 g, 17.31 mmol) in CH2Cl2 (56 mL) @ 0° C. under N2 was added SOCl2 (3.09 g, 25.97 mmol). The mixture was then allowed to warm to rt and stirred for 3 hr. The mixture was then cooled back to 0° C. and quenched with saturated aqueous sodium bicarbonate. The resulting mixture was extracted 3× with CH2Cl2. The combined organics were dried (Na2SO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography (25-35% CH2Cl2 in Hexanes) to give 2-bromo-6-[chloro(6-methoxypyridin-2-yl)methyl]pyridine. 1H NMR (500 MHz, CDCl3) δ 7.76 (d, 1H, J=7.8), 7.61-7.54 (m, 2H), 7.41 (d, 1H, J=7.8), 7.12 (d, 1H, J=7.1), 6.66 (d, 1H, J=8.3), 6.02 (s, 1H), 3.86 (s, 3H), LRMS m/z (M+H) Calcd.: 313.0, found: 312.9.

Workup

  1. custom@ 0° C. under N2
  2. temperatureThe mixture was then cooled back to 0° C.
  3. customquenched with saturated aqueous sodium bicarbonate
  4. extractionThe resulting mixture was extracted 3× with CH2Cl2
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel chromatography (25-35% CH2Cl2 in Hexanes)

Sources & evidence

ORD record
ord-05c274f6235f4a28bde01918cdbc80b5
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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